Collective Syntheses of Corynanthe Alkaloids Based on a Chirality-Tunable Structure Unit

A novel strategy based on a common intermediate bearing a chirality-tunable structure unit for the collective syntheses of corynantheine-type and heteroyohimbine-type alkaloids has been developed. Key transformations of the synthetic strategy are a sequential nucleophilic C–N bond formation/Mannich-...

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Bibliographic Details
Published in:Organic letters 2024-10, Vol.26 (41), p.8803-8809
Main Authors: Liu, Tongqi, Huang, Zhenrui, Cheng, Shuai, Chen, Wen, Yang, Xiaodong, Zhang, Hongbin
Format: Article
Language:English
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Summary:A novel strategy based on a common intermediate bearing a chirality-tunable structure unit for the collective syntheses of corynantheine-type and heteroyohimbine-type alkaloids has been developed. Key transformations of the synthetic strategy are a sequential nucleophilic C–N bond formation/Mannich-type cyclization to construct the highly functional C/D rings, a stereocontrolled introduction of the C15 and C20 chiral centers based on the chirality-tunable structure unit, and an amine-directed addition of Me3Al to construct the C18 methyl group.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03177