Escuela de Ciencias de la SaludUniversidad Autónoma de Baja California

Group Meeting Presentation

Jesus Cordova GuerreroOlson Research Group

May 27th, 2016

Reports on the Total Synthesis of Ibogaine

University of California Davis

Escuela de Ciencias de la SaludUniversidad Autónoma de Baja California

University of California Davis

Ibogaine: structure and biological activity

2

Tabernanthe or Tabernaemontane

species

Apocynaceae family

NH

NMeO

Me

1) Monoterpene indole alkaloid: indole + isoquinuclidine + 7-membered azepane

2) Biology:

• Potent psychoactive agent• Demethylation – noribogaine• Antifungal, antilipase, anti HIV, anti-cholinesterasic activity

Escuela de Ciencias de la SaludUniversidad Autónoma de Baja California

University of California Davis

Ibogaine: total syntheses

3

NH

NMeO

Me

1966, Ziegler et al.Buchi, G.; Coffen, D. L.; Kocsis, K.; Sonnet, P. E.; Ziegler, F. E. J. Am. Chem. Soc.1966, 88, 3099.

2012, Sinha et al.8 steps, 9.8% overall yield

Jana, G.K.; Sinha, S. Tetrahedron 2012, 68, 7155-7165.

2016, She et al.12 steps, 14.5% overall yield

Gaoyuan Zhao, G.; Xie, X.; Sun, H.; Yuan, Z.; Zhong, Z.; Tang, S.; She, X. Organic Letters 2016 18 (10), 2447-2450 .

2016, Olson et al.7 or less steps, ?% overall yield

Escuela de Ciencias de la SaludUniversidad Autónoma de Baja California

University of California Davis

Total synthesis of ibogaine by She et al.

4

(±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D

Escuela de Ciencias de la SaludUniversidad Autónoma de Baja California

University of California Davis

Total synthesis of ibogaine by She et al.

5

Synthesis of tabertinggine and 12-methoxy tabertinggine advanced intermediate

Escuela de Ciencias de la SaludUniversidad Autónoma de Baja California

University of California Davis

Total synthesis of ibogaine by She et al.

6

Synthesis of (±)-ibogamine

Total synthesis of ibogaine by She et al.

Synthesis of (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D

Escuela de Ciencias de la SaludUniversidad Autónoma de Baja California

University of California Davis

Total synthesis of ibogaine by Sinha et al.

8

Escuela de Ciencias de la SaludUniversidad Autónoma de Baja California

Thank you

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