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Asymmetric Synthesis of cis-3α-Aryloctahydroindole Alkaloids by Ene-Reductase Dehydrocyclization
Jianjiong Li1,2, Siyu Li1,3, Yu Wang1
1National Center of Technology Innovation for Synthetic Biology, National Engineering Research Center of Industrial Enzymes and Tianjin Engineering Research Center of Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, 32 Xi Qi Dao, Tianjin Airport Economic Area, Tianjin 300308, China.
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.
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