Bioinspired Total Synthesis of Montanine-Type Amaryllidaceae Alkaloids

Finding a common path: A synthetic strategy inspired by the proposed biogenesis of the montanine‐type alkaloids enabled the concise asymmetric synthesis of these compounds in a divergent fashion on the basis of an unprecedented tandem oxidative dearomatization/intramolecular aza‐Michael addition as...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2013-12, Vol.52 (52), p.14167-14172
Main Authors: Bao, Xu, Cao, Ye-Xing, Chu, Wen-Dao, Qu, Hu, Du, Ji-Yuan, Zhao, Xian-He, Ma, Xiao-Yan, Wang, Cheng-Tao, Fan, Chun-An
Format: Article
Language:English
Subjects:
Alkaloids
Alkaloids - chemistry
Amaryllidaceae Alkaloids - chemical synthesis
Amaryllidaceae Alkaloids - chemistry
Asymmetry
bioinspired synthesis
dearomatization
domino reactions
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Strategy
Synthesis
total synthesis
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Summary:Finding a common path: A synthetic strategy inspired by the proposed biogenesis of the montanine‐type alkaloids enabled the concise asymmetric synthesis of these compounds in a divergent fashion on the basis of an unprecedented tandem oxidative dearomatization/intramolecular aza‐Michael addition as the key step. This bioinspired approach revealed a chemical connection between the cherylline‐ and montanine‐type alkaloids (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201307324