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Bioinspired Synthesis of Nortriterpenoid Propindilactone G
Yu Wang1, Bo Chen1, Xubiao He1
1CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Abstract:
A concise bioinspired synthesis of Schisandra nortriterpenoid propindilactone G has been accomplished from a readily accessible steroidal lactone. Key transformations include a Breslow remote functionalization, a Suárez remote radical functionalization, a ring expansion enabled by a Wagner-Meerwein rearrangement, a stereoinversion of a tertiary alcohol, and a biomimetic transesterification/oxa-Michael addition cascade. This work also provides experimental evidence of the putative propindilactone G biosynthesis pathway.
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