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Page 1: Total Synthesis of Arboridinine - qigroup.nibs.ac.cnqigroup.nibs.ac.cn/wp-content/uploads/2019/03/Total-Synthesis-of-Arbor... · J. Am. Chem. soc. XXXX, XXX, XXX-XXX [UI RIS Citation

Total Synthesis of Arboridinine

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Features of Arboridinine

isolated in 2015

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Representative Alkaloids Sharing Similar Patterns with Arboridinine

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Retrosynthetic Analysis of Arboridinine

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Racemic and EnantioselectiveSyntheses of the Tricyclic Core

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Org. Lett. 2010, 12, 3104-3107

J. Am. Chem. Soc. 2011, 133, 1772–1774

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Screening of Conditions To Enantioselectively Acetylate Diol 17

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Completion Total Synthesis of Arboridinine

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Angew.Chem.Int.Ed.2015,54,9546–9549

Angew.Chem.Int.Ed.2016,55,13798–13802

Ag-Based 6-endo Dig Cyclization of 12

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Strategic Disconnection of Arboridinine

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Investigation of Double-Mannich Cyclization

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Construction of Bicyclic Indole Framework

Tetrahedron 2012, 68, 1017-1028

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Synthesis of Deoxyarboridinine

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Transformation of Ketone (Aldehyde) Into Alkene

Wittig reaction

Horner-Wadsworth-Emmons olefination (HWE olefination)

Tebbe olefination/ Petasis-Tebbe olefination

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Julia-Lythgoe olefination

Peterson olefination

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Takai-Utimoto olefination (Takai reaction)

Takai-Lombardo Reaction

Takeda Olefination Org. Lett. 2004, 6, 4961

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Nysted reagent

P: Wittig, HWETi: Tebbe, Petasis, Takai-Lombardo, Takeda, McMurryS: Julia Si: PetersonCr: Takai-UtimotoZn: Nysted

Bamford-Stevens-Shapiro reaction

McMurry coupling

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Revised Retrosynthetic Analysis

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Studies of Asymmetric Michael Addition

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Total Synthesis of (+)-Arboridinine

Org. Lett. 2015, 17, 4476-4478

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13-step racemic synthesis and 16-step formal asymmetric synthesis

14-step asymmetric total synthesis

Comparison between these Two Syntheses

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