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Total Synthesis of (+)‐Alsmaphorazine C and Formal Synthesis of (+)‐Strictamine: A Photo‐Fries Approach
Author(s) -
Gao Beiling,
Yao Fengjie,
Zhang Zhaodong,
Ding Hanfeng
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202101752
Subject(s) - imine , formal synthesis , monoterpene , continuous flow , indole test , combinatorial chemistry , total synthesis , cascade , divergent synthesis , chemistry , stereochemistry , organic chemistry , biochemical engineering , catalysis , engineering , chromatography
A bioinspired photo‐Fries/imine capture cascade reaction was developed in continuous‐flow mode, which facilitated the rapid construction of a series of diversely functionalized 2,7‐heterocycle‐fused tetrahydrocarbazoles, the ubiquitous core structures embedded in strychnos and akuammiline‐type monoterpene indole alkaloids. The synthetic utility of this novel method has been preliminarily explored by the first total synthesis of (+)‐alsmaphorazine C and formal synthesis of (+)‐strictamine in a concise and efficient manner.