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Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

ABSTRACT: A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (-)-zephyranthine. The concise route includes a catalytic Michael/Michael cascade for the asymmetric synthesis of a penta-substituted cyclohexane with three contiguous stereogenic centers, a remarkable 8-step one-pot operation to easily assemble the zephyranthine tetracyclic skeleton, the regioselective construction of a double bond in the C ring and an asymmetric dihydroxylation. This synthesis is also flexible and paves a potential path to a variety of cyclohexylamine-fused tricyclic or polycyclic alkaloids.

SUBMITTER: Zhao Y

PROVIDER: S-EPMC8278928 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

Zhao Yuxiang Y Zhu Yanren Y Ma Guolan G Wei Qi Q Yang Shaoxiong S Zeng Xiaoyu X Zhang Hongbin H Chen Jingbo J

Chemical science 20210621 27

A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (-)-zephyranthine. The concise route includes a catalytic Michael/Michael cascade for the asymmetric synthesis of a penta-substituted cyclohexane with three contiguous stereogenic centers, a remarkable 8-step one-pot operation to easily assemble the zephyranthine tetracyclic skeleton, the regioselective con ...[more]

PMID: 34349919

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