Shoppee Charles William 1904-1994

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doi: 10.1098/rsbm.2003.0029, 495-507492003Biogr. Mems Fell. R. Soc.

Lewis N. Mander 20 October 1994Charles William Shoppee. 4 February 1904

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CHARLES WILLIAM SHOPPEE

4 February 1904 20 October 1994

Biogr. Mems Fell. R. Soc. Lond. 49, 495507 (2003)

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EARLY YEARS

Charles Shoppee was born on 4 February 1904, at Crouch End (a northern suburb of London),

the elder son of Joseph William and Emma Elizabeth Shoppee (ne Hawkswell of York).

Charless younger brother, Stanley Shoppee (later FCA), predeceased him in 1967. The fam-

ily was descended from the noble French family of Chappuis, and could trace its ancestry back

to 1109. The male members of the family were generally pillars of the Church or lawyers

often Clerk of the Parlement at Lyon, although Louis Chappuis was created Marquis de

Mirebel by letters patent of Louis XV of France in 1746. An earlier, female member of the

family was distinguished by her descendants, being the great-grandmother of Armand Jean du

Plessis, Cardinal Duc de Richelieu, and the great-great-grandmother of the Duc de Villars,

Marshal of France.

Although Joseph Shoppee was only four years old when his own father died, he nevertheless

went on to Kings College, London, where he won several prizes. However, after two years

financial circumstances caused him to enter the office of John K. Gilliat and Company of 7

Crosby Square, London. There he remained for the rest of his life (d. 15 August 1944), eventu-

ally becoming secretary to the company. Joseph Shoppee was a man of varied intellectual attain-

ments; readily reading French and German, he rapidly learnt Spanish when his company entered

the Costa Rica coffee market. Although he had not looked at conic sections and trigonometry for

some 35 years, he still knew these subjects well when Charles encountered them. The father was

interested in French, German and Italian medieval history, and was well acquainted with

medieval architecturehe had visited every cathedral in England and Wales several times. As a

species of counterweight to this medievalism, he was also interested in the topography of the

railways of England, Scotland and Wales. Thus, Charles grew up in a stimulating environment.

At the age of 10 years, Charles went to the Stationers Companys School, where he flour-

ished. He eventually became captain of football, captain of cricket, sergeant-major of theOfficer Training Corps, school organist, head prefect, and captain of the school. At about the

age of 13, he showed promising talent as a pianist and could struggle (his words) through the

Scherzo in B flat minor (op. 31) of Chopin. He studied with Dr R. Walker Robson, acquired

the Matthey technique, and gradually became acquainted with some of the works of Bach,

Mozart, Beethoven, Chopin, Schumann, Liszt, Brahms, Csar Franck, Scriabin and

Rachmaninov. At school, he was greatly influenced by two of the masters, A.E. Richards BA

(Cantab.) (Mathematics) and F.T. Addyman, BSc (Lond.), FRIC (Chemistry), eventually pass-

ing the Intermediate Examination of the University of London with honours in 1921.

On leaving school in 1921, Oxford or Cambridge being financially impossible, Shoppee

went to Imperial College (Royal College of Science), where he obtained the ARCS in 1923

and majored in chemistry with first-class honours. In his year were H.J. Emeleus and

R.P. (later Sir Reginald) Linstead, both later to be elected to the Fellowship of The RoyalSociety (in 1946 and 1940, respectively), as was Charles. During the year 192324, he became

a research student of Sir Jocelyn Thorpes, and tried to repeat some work on citraconic anhy-

dride said to yield a cyclobutane compound. In fact, the main product, derived by three-car-

bon tautomerism from itaconic anhydride, was a derivative of cyclopentane. During his years

at college, Charles played association football (soccer) for the Royal College of Science and

Imperial College, and cricket for the Highgate Cricket Club. He also managed to continue

playing the piano and the organ, and even managed to earn some useful pocket money by tak-

ing services when the church organist was absent on his summer holiday.

498 Biographical Memoirs



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EARLY CAREER

In 1924 Christopher (later Sir Christopher) Ingold FRS was elected to the Chair of Organic

Chemistry at the University of Leeds and invited Shoppee to accompany him, obtaining for

him a Department of Scientific and Industrial Research grant of 120 a year. Charless mother

had been, before her marriage, a teacher at a school in Kirkstall, near Leeds, and he had distant

relatives in Wharfedale who were tenant farmers of Lord Harwood. They lived in a delightful

old farmhouse, dating from 1577, called The Nunnery at Arthington. He often used to walk to

or from Arthington on Sundays and get a good lunch.

At Leeds with Ingold, Charles continued the work, begun with Thorpe, on tautomerism and

reaction mechanism, but he never became involved in the IngoldRobinson controversy on

aromatic nitration. He played soccer for the University of Leeds and in 1926 his team won the

Christie Cup in competition with the universities of Manchester and Liverpool for the first

time in 15 years; he was elected captain in 1928. He played twice for the combined Northern

Universities XI before the International Selection Committee, but to his disappointment he

never secured an England cap. Leeds was an excellent centre for music and he had the good

fortune to hear performances by Rosenthal, Hoffmann, Backhaus, Rubinstein, Moiseiwitch,

Brailowsky, Cortot, Solomon, Smeterlin, Rachmaninov, Curzon and Paderewski (who at the

time was Prime Minister of Poland). In 1926 he was awarded a Senior Research Studentship

of the Royal Commission for the Exhibition of 1851 and for a variety of reasons decided to

hold the award at Leeds instead of going to Europe. In the summer of 1929 he became a

demonstrator in organic chemistry at Leeds, and on the strength of this appointment he

married Eileen West on 18 July 1929. Eileen was later found to be a distant cousin of Margery

Bell (ne West), the wife of the eminent physical chemist R.P. Bell (FRS 1944). Eileen

Shoppee was from Leeds and was in her youth a fine tennis playerof Yorkshire County

standingwhile Charles himself was still playing competitive tennis in the Langland tourna-ment in Swansea two decades later.

In 1930, Ingold left Leeds for University College London, and Shoppee and several other

students were left (in their words) high and dry in the provinces. He obtained his DSc

(London) in 1931, and was promoted to Assistant Lecturer in 1936. He made several attempts

to move from Leeds during the period 193138, but junior academic posts were in short sup-

ply after the financial crisis of 1930 and the subsequent Depression. On a visit to the

University of Manchester, he had the good fortune to meet I.M. (later Sir Ian) Heilbron, FRS,

and told him that he was stranded in Leeds. On Heilbrons advice, he persuaded the University

of Leeds to nominate him for a Rockefeller Research Fellowship in 1938. In the spring of

1939, on the very same day, he received two letters: one offering him a Leverhulme Research

Fellowship at the University of Oxford for two years, the other offering him a Rockefeller

Research Fellowship for one year at any university that he cared to select. Eventually hedecided, with some heartache, to accept the Rockefeller invitation, and then there arose the

question of where to go. He decided against Harvard or Yale as perhaps being too much like

England, and was tempted to go to Adolf Butenandt (ForMemRS 1969) at the Kaiser Wilhelm

Institut in Berlin, but his wife considered it would be too dangerous. He then thought of going

to Leopold Ruzicka (ForMemRS 1942) in Zurich and sought the advice of Heilbron, who

pointed out that Ruzicka had a very large research group and that Shoppee would see little or

nothing of the great man, whereas Reichstein had left Zurich in 1938 for Basel and had a rel-

atively small research group. So Charles, with his wife and six-year-old daughter, proceeded

Charles William Shoppee 499



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to Basel. The move was to shape his science for the future as he combined his Ingoldian her-itage of mechanistic organic chemistry with his freshly acquired skills in steroid chemistry to

excellent effect.

BASEL, 193845, AND LONDON, 194548

On 3 September 1939 Charles listened with dismay, but without surprise, to Neville

Chamberlains broadcast declaring war on Germany and at once wrote to the Vice-

Chancellor of the University of Leeds offering to resign his Research Fellowship and return

home; but he was instructed to continue his work unless he received other instructions from

the British Consulate-General in Basel. During the winter of 1939 and the spring of 1940 he

worked with Reichstein on the structures of the adrenocortical steroid hormones andcompleted some of his best experimental work. He acquired Reichsteins micro-technique

and learnt how to do column chromatography with colourless, non-fluorescent compounds.

At Whitsuntide in 1940, with war news getting worse and worse, the family attempted to

return to England, but their French visas never came through and they were compelled to

remain in the largest and most beautiful concentration camp in Europe, namely

Switzerland, for six years. His contribution to the war effect was accordingly confined to

collecting news about Germany and to gathering specimens of petrol from German lorries

in Basel and analysing the samples.

In 1944, Charles was appointed, in absentia, through the good offices of Sir Ian Heilbron,

to a Readership in Chemistry in the University of London, tenable at the Royal Cancer

Hospital (now the Royal Marsden Hospital). After a nightmarish journey from Basel to

London, taking three days and zigzagging across the Channel in a very small steamerThe Isle

of Thane, he took up his Readership in May 1945 and the family was able to celebrate VE Day

in London. At the Royal Cancer Hospital he worked on the steroid constituents of the

unsaponifiable extract of human Bantu livers, but could isolate only cholesterol and its oxida-

tion and dehydration products.

SWANSEA, 194856

In 1948 Shoppee was appointed to the Chair of Chemistry in the University of Wales at the

University College, Swansea, succeeding J.E. Coates, a physical chemist. He continued the

application of reaction mechanism to the determination of configuration of steroids with some

success, and was elected to the Fellowship of The Royal Society in 1956. By present stan-

dards, the 1948 Swansea Department of Chemistry would be regarded as far too small adepartment to give an adequate training in chemistry or opportunities for research. Charles had

five members of staff, together with a full-time demonstrator. (Three of the five subsequently

became professors, and the demonstrator founded a special chemicals company.) In his eight

years in Swansea the department produced about 130 honours graduates in chemistry, and

from these a vigorous research school developed. Current orthodoxy suggests that the number

of postgraduates would be inadequate for a viable research training, but such a view is hardly

tenable, given that the Swansea department produced six professors (R.J.W. Cremlyn,

W.O. George, D.H. Richards, M.W. Roberts, J.M. (later Sir John Meurig) Thomas (FRS 1977)




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and W.J. Thomas), as well as a polytechnic director (D.W.F. James) and several universityreaders and senior lecturers. Shoppee was able to generate enthusiasm among his staff and stu-

dents. He had a genial, friendly disposition and was ready to ask his most junior colleagues

for their advice on research problems. In the teaching of chemistry he had a favourite adage,

there are not three chemistries, organic, inorganic and physical, but just onechemistry

itself. He consequently supported the research interests of all his colleagues with students and

finance for apparatus and expensive chemicals, despite the fact that the departmental funding

was generally hard pressed. He was also ready to listen to the beginning research students and

to accept their choice of research topic and supervisor, even when this did not coincide with

his own inclinations. He was often accompanied by his dog, Wally, and a member of the tech-

nical staff would be requested to exercise the dog in the adjacent park. It was not uncommon

to see Shoppee returning to his home for lunch as a pillion rider on a motorcycle driven by a

member of the technical staff, with the dog occupying an intermediate position.

SYDNEY, 195669

However, the damp climate of Wales affected Eileen Shoppees health and, after she had suf-

fered a long series of upper respiratory tract ailments, Charles was advised by former col-

leagues in Harley Street to seek a warmer and sunnier climate for her. He therefore accepted

an invitation to the Chair of Organic Chemistry at the University of Sydney at the end of 1956,

after the resignation of Arthur Birch (FRS 1958), who left Sydney for Manchester. When his

emigration to Australia became known, Shoppee was jokingly asked, in view of his stereo-

chemical interests, whether going down-under would entail an inversion of nomenclature.

After some pondering he realized that it was the subject of a joke. The Sydney sunshine

restored his wifes health and they began to enjoy the beauties of a new and fascinating

continent.

The early part of Shoppees tenure at Sydney coincided with the relocation of the School

of Chemistry from its rather ramshackle accommodation in the Science Road of the University

to the modern building in Western Avenue, where it remains to this day. More importantly, his

tenure coincided with the period of expansion and flowering of Australian universities, to

which he made major contributions. Shoppee continued to apply reaction mechanistic

concepts and new techniques to structure determination in natural products, mainly within the

context of steroid chemistry, a major part of the work being pursued in collaboration with

Associate Professor Ruth E. Lack. Shoppee was elected a Fellow of the Australian Academy

of Science in 1958, and served as a member of its Council from 1959 to 1962 and as a Vice

President from 1961 to 1962). Although Shoppee never sought administrative positions within

the University of Sydney, he was throughout his tenure the head of the Department of Organic

Chemistry by virtue of his appointment as professor, and he worked conscientiously and suc-cessfully on behalf of his department with the invaluable help of Ern Ritchie FAA, who was

to succeed him as Professor of Organic Chemistry in 1969. Shoppee also served a period as

Dean of the Faculty of Science (196667) and, although this position was far less central than

it is at present, he rendered distinguished service to the Faculty in this capacity. He benefited

from the former isolation of Australia that had made sabbatical leave much more accessible

than in the UK. Thus, he was able to visit the USA and the UK every two years. These peri-

ods of leave proved extremely stimulating, and in 196768 he learnt about the

WoodwardHoffman rules, and recognized that some of his early work with Ingold at Leeds




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in 1928 had involved the thermal ground-state cycloaddition of a pentadienyl cation. A paperto this effect appeared in 1969, the year of his retirement, thereby closing the circle on a

remarkable career.

POST-RETIREMENT, 197094

He was compulsorily retired at the age of 65 after a year rendered very difficult by the need

to become acting head of the School of Chemistry as a consequence of the illness of his senior

professorial colleague, R.J.W. Le Fvre FRS, and the subsequent illness and death of his junior

professorial colleague, A.E. Alexander FAA. However, associates in the USA had heard that

he would be available in 1970, and he was offered the Foundation Welch Professorship of

Chemistry at Texas Technological University (Lubbock, Texas), which he took up in January1970 for a period of five years. He continued some steroid work, but concentrated the main

effort of his group on the cycloadditions of penta-1,4-dienyl cations. He retired from the

Welch Chair in 1975, and he and his wife returned to Australia to be closer to their daughter,

Adrienne Horrigan, her husband, William, and their four grandchildren. After a period as an

honorary professorial fellow at Macquarie University (197679) Charles moved to Melbourne

to be closer to his family, after the death of his beloved Eileen. He was appointed an honorary

visiting professor at La Trobe University in 1980 and maintained his research interests into his

middle 80s, working at the bench for one day each week until the age of 87. In his letters he

noted that the university encouraged him to waste their money on his chemicals so that he

could pursue some long-standing interests.

SCIENTIFIC WORK

Prewar period, 192139

After Shoppee graduated from the University of London, he was invited by Christopher

Ingold, the doyen of UK physicalorganic chemists to join him at the University of Leeds,

where he had just accepted a chair in chemistry. Ingolds influence on the whole of organic

chemistry was enormous and clearly left its mark on Shoppee. Although Shoppee was to

devote most of his future research to the chemistry of steroids, the emphasis was very much

on mechanism and more physical aspects: among others, he published a series of 70 papers on

Steroids and Walden inversion (see below). Late in his career he was to become ever more

preoccupied with structure and mechanism. At Leeds he continued the work, begun with

Thorpe, on tautomerism and reaction mechanisms until Ingolds return to London. Later,

during the period 193138, he extended these studies to various cyclopentenes, publishing aseries of papers jointly with Harold Burton.

Basel, 193945

Supported by a Rockefeller Research Fellowship, Shoppee decided to join Tadeus Reichsteins

group at Basel in the spring of 1939, a fateful decision in several respects. The adrenal glands

of mammals comprise two sharply differentiated regions, the medulla producing ()-adrena-

line, and the cortex elaborating several hormones essential to life. Absence of these hormones,

after destruction of the glands by tubercular infection (Addisons disease) or bilateral adrena-




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lectomy, was shown to lead to multiple insufficiency symptoms and death. In about 1930,adrenocortical extracts were prepared, which by daily injection were capable of maintaining

patients with Addisons disease and adrenalectomized animals alive for practically unlimited

periods. It was at first thought that the biological activity of such extracts was due to a single

substance, but during the period 193560 47 compounds were isolated. Eight of these com-

pounds are highly active, including cortexone, aldosterone, cortisone and cortisol, this last

being the most important adrenocortical hormone. Four groups of workers were engaged in

the isolation of individual compounds, 31 of which were discovered by the Reichstein group.

Milligram amounts of individual steroids were isolated from half a tonne of adrenal glands

that had been obtained from 20 000 cattle. Shoppee discovered that the inert 11-oxygen func-

tion, characteristic of the adrenocorticoids, could be smoothly removed as an axial 11-

hydroxyl group by acid-catalysed dehydration. Subsequent conversion into known steroids

provided the first direct structural correlation for these compounds.Reichstein and Shoppee also worked on the structures of cardiotonic glycosides and their

aglycones. Certain steroidal glycosides isolated from plants possess powerful cardiotonic

activity. Acidic or enzymatic hydrolysis affords the steroid aglycones or genins. The cardio-

tonic property is associated with the special structure of the aglycone but is modified in regard

to solubility and transport by the nature of the conjugated sugars. Use of digitalis in heart

therapy was introduced in 1785 by the Scottish physician William Withering and met with

spectacular success. Administration in cases of impaired heart function leads to decreased rate

and increased intensity of the heart beat, whereas overdosage produces systolic stoppage of

the heart. In addition to use in cardiotherapy, some glycosides have been used as drugs in

trials by ordeal and as arrow poisons. The free aglycones are convulsive poisons rather than

heart stimulants and are of little medicinal value. The main sources of the glycosides are plants

of the Apoeynaceae, Liliaceae, Ranunculaceae and Scrophulariaceae; certain species of

Digitalis (foxglove) furnish most of the drugs of therapeutic value.Shoppee and Reichstein worked on the structure of diginin, isolated from leaves of

Digitalis purpureaby Karrer in 1936, which was actually devoid of cardiac activity; 13 g of

glycoside was supplied by Hoffmann LaRoche. By a series of transformations, including

WolffKishner reduction and hydrogenation, Shoppee was able to degrade the derived

aglycone, diginigenin, to the parent hydrocarbon, which was not identical with any hydrocar-

bon known at the time, and arrived at the tentative formula 1. An intermediate diketone was

later identified by Press and Reichstein by synthesis as 5,14,17-pregnane-3,20-dione. This

evidence established the steroid nature of diginigenin and the location of oxygen functions at

C-3 and C-20. However, it was another two decades before Shoppee, in collaboration with

Ruth Lack and Alex Robertson at the University of Sydney, established the correct structure

as 2 with the benefit of NMR data. In 1943, with Reichsteins approval, Shoppee started to

apply reaction mechanistic concepts to the reactions of natural products, and particularly


O

HO

O

O

H

H H

HO

O

O

O

H

H

H

H

(1) (2)



11/15

steroids, with which he was in the vanguard of a huge and widespread activity prompted in

part by the pharmaceutical industrys interests in these important compounds.

Postwar period, 194548

In May, 1945 Shoppee took up a Readership in Chemistry in the University of London and

was based at the Royal Cancer Hospital. While there, he initiated his remarkable series of 70

papers on Steroids and the Walden inversion, the latter term describing a process (which

would now be labelled as SN

2 substitutionsee figure 1) in which a group attached to an

organic molecule is replaced by another group with inversion of the configuration of the

carbon atom bearing the leaving group.

In practice, the title of the series was a convenient label for wide-ranging explorations of

structure, stereochemistry and mechanism. Ironically, much of the chemistry described in thevery first paper involved the retention of configuration rather than inversion. At the time there

was considerable controversy over the conformation (shape) of the six-membered cyclo-

hexane ring and compounds containing this structure. Two major conformations are possible

(figure 2). One is a rigid puckered shape described as a chair in which carbons 2,3 and 5,6 are

coplanar, with C-1 above this plane and C-4 below. The second conformation is quite mobile

and has C-1 and C-4 both above the plane; it is described as a boat. Shoppee calculated that

the barrier between the two conformations should be ca. 10 kcal mmol1, a remarkably close

estimate to the now established value of 11 kcal mmol1. D.H.R. (later Sir Derek) Barton

(FRS 1954), with whom Shoppee later published a brief communication on the conformation

of cyclohexene, received the Nobel Prize for his research in this area.

Swansea, 194856

Shoppee was invited to the Chair of Chemistry in this small but vigorous department.

However, as in much of the UK, not much research had been done during the war and its

aftermath. He set about building it up and was to enhance its standing considerably. He

continued his research on steroids, a significant part of it in collaboration with G.H.R.

Summers, publishing prolifically on transformations applied to various parts of these molec-

ules. In addition to continuing the Walden inversion series, he also began in 1952 a new

series of (ultimately) 39 papers on broader aspects of steroid chemistry. One special interest

was the behaviour of 5-3-hydroxy steroids (a major feature of cholesterol). From his


Y-

a

X

c

b

a

Y

c

b X-+

Figure 1

12

3

4 56

Figure 2



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earlier work at Leeds with Ingold, Shoppee recognized that in substitution reactions at C-3,

the 5-ene bond was participating in the reaction (partial bonding between C-3 and C-5) so

that retention rather than the more normal inversion prevailed. Under the right conditions, a

bond is actually formed between C-3 and C-5 with the addition of a ligand to C-6 to form ani-steroid (figure 3).

Again, we should note that although such changes would be obvious with the benefit of

modern spectroscopic techniques, it was a triumph of analytical reasoning to deduce such

changes in their absence. And although the results from these and other studies pursued by

Shoppee and his co-workers were of vital importance to our knowledge of steroid chemistry,

they also informed wider areas of endeavour in our understanding of modern organic chem-

istry. During this period, he published more than 65 articles and original papers, the value of

which was recognized in 1956 by his election to the Fellowship of The Royal Society.

University of Sydney, 195669

Arriving in Sydney must have been a terrible shock for Shoppee. It was before the Murray

Report in 1957 that was to revolutionize the funding and organization of Australian universi-ties under Commonwealth auspices (with enormous resistance from the individual states).

Research funding and modern equipment for organic chemists were almost non-existent; there

was not even an infrared spectrometer in the Organic Chemistry Department, and it was nec-

essary to plot ultraviolet spectra by hand. Shoppees predecessor, Arthur Birch, had departed

for a chair at Manchester in sheer frustration, prompting newspaper headlines referring to

Beggars in mortarboards. David Craig (FRS 1968) and Ronald (later Sir Ronald) Nyholm

(FRS 1958) left soon afterwards, reinforcing the message, although Birch and Craig were to

return in 1967 to found the Research School of Chemistry at the Australian National

University. Nyholm participated in the planning, but elected to remain in the UK.

Nevertheless, Shoppees research on steroids prospered. He continued his interests in the

bromination of steroidal ketones, but branched out to modification of various steroidal skele-

tons and the insertion of nitrogen into various rings in a search for interesting biological activ-

ity. His research was given a considerable boost with the arrival of modern spectrometric

methods (for organic chemists) and he enthusiastically embraced these new techniques, espe-

cially nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (in addition to

ultraviolet and infrared spectroscopy, which had finally been established at Sydney). The

techniques were liberating and, among other objectives, Shoppee revisited long-standing

problems, finally deriving definitive structures for several steroidal sapogenins, including

diginigenin (see above), digifologenin and digacetigenin. With the publication of the

WoodwardHoffman rules in 1964, the principles underlying huge tracts of hitherto poorly


ArSO2O

H

H H

R

X

H

H H

R

X

3 5

-

Figure 3



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understood organic mechanisms were revealed. For Shoppee it was intoxicating, and he revis-ited the research that had been undertaken with Ingold and then Burton, finally achieving a

full understanding of the processes involved.

Texas Technological University, 197074

After his retirement from Sydney University, Shoppee moved to a chair at Texas Tech, where

he continued his interests in electrocyclic processes, publishing a dozen or so papers in this

area. He was especially interested in re-examining the thermal ground-state [2s+2

a] con-

rotatory cycloadditions of penta-1,4-dienyl cations, the photochemical excited-state

[2s+2

s+2

s] disrotatory cycloaddition of a penta-1,4-dienide anion, and some photo-

chemical excited-state [2s+2

s] or [2

a+2

a] disrotatory cycloadditions of penta-1,4-

diene molecules.

Retirement years, 197594

Shoppee returned to Australia in August 1975 and took up an appointment as an honorary pro-

fessorial fellow at Macquarie University (197679), then moved to Melbourne to be closer to

family after the death of his wife. Shoppee was appointed an honorary visiting professor at La

Trobe University in 1980 and maintained a vigorous interest in chemistry until his death on 20

October 1994, aged 90. As a measure of his fascination with chemistry, he was still working

at the bench at the age of 87.

CONCLUSION

We should place Shoppees scientific achievements into context. Contemporary organicchemists enjoy the enormous benefits of spectroscopic techniques and separation methods that

became available only towards the end of Shoppees career. Without these aids most modern

practitioners would not know where to begin, and yet it was a field in which he excelled,

especially the assignment of stereochemistry. Problems that could now be solved in a few min-

utes by a first-year undergraduate, using NMR spectroscopy, would have taken Shoppee and

his colleagues several months or even longer. The availability of reagents was extremely

limited and very few were commercially available. From a modern perspective it is difficult

to understand how it was possible to isolate and deduce the structures of organic molecules,

especially those as complex as the adrenocortical steroid hormones, before the availability of

NMR spectroscopy in the late 1950s. And yet chemical and some limited physical methods

were sufficient for Shoppee and his co-workers until the arrival of the first NMR spectrometer

(a Varian A60) at Sydney in 1962. The advent was almost too late for Shoppee, but it was aturning point for those of us that followed. In 1998, the University of Wales at Swansea

launched the C.W. Shoppee Memorial Appeal to fund scholarships for entering chemistry

students. Students from all over the world are eligible, reflecting the international nature of the

career pursued by Shoppee,




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ACKNOWLEDGEMENTS

I am most grateful to William Horrigan, the late Sir Ewart Jones FRS, Brian Gowenlock, John Davies and R.H. Davies

for providing material relating to the earlier stages of Shoppees career, and to Sever Sternhell and Henry Shine for

information on the later years.

The frontispiece photograph is reproduced by courtesy of the Victoria and Albert Museum. Copyright Victoria

and Albert Museum Archives.

BIBLIOGRAPHY

A full bibliography appears on the accompanying microfiche. A photocopy is available from

The Royal Societys Library at cost.




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Documents

Shoppee Charles William 1904-1994