Asymmetric Synthesis of cis -3α-Aryloctahydroindole Alkaloids by Ene-Reductase Dehydrocyclization

Organic Letters 2026

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Authors: Jianjiong Li, Siyu Li, Yu Wang, Jinhui Feng, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
DOI: 10.1021/acs.orglett.5c05242
Cited by: 0
References: 36

Abstract

In this study, an unprecedented, enzymatic, and enantioselective desymmetrization and cyclization reaction of achiral 4,4-disubstituted cyclohexanones has been developed for the asymmetric synthesis of cis -3α-aryloctahydroindole alkaloids bearing an all-carbon quaternary stereocenter as well as a tertiary carbon stereocenter. Using different ene-reductases as the biocatalysts, a variety of 3α-aryloctahydroindoles have been obtained in high yields (71–90%) and excellent enantioselectivities (>99% ee), providing an efficient strategy to prepare these important alkaloids.

Fields of Study & Subjects

Asymmetric Synthesis and Catalysis Enzyme Catalysis and Immobilization Asymmetric Hydrogenation and Catalysis

Publication details

Journal / source
Organic Letters
Volume
28
Issue
5
Pages
1738–1743
Publication date
27 January 2026
Language
EN