A C-H Functionalization Strategy Enables an Enantioselective Formal Synthesis of (-)-Aflatoxin B2
Nicholas A Falcone1, Aaron T Bosse2, Hojoon Park3
1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
Abstract:
An enantioselective formal synthesis of (-)-aflatoxin B2 from 4-methoxyphenylacetic acid has been achieved by an approach that produces a key carbon-carbon bond, a benzylic stereocenter, and two arene carbon-oxygen bonds in the course of three site-selective C-H functionalizations. The carbonyl-directed acetoxylation of two arene C-H bonds described herein is unprecedented in natural product synthesis and occurs under mild conditions that preserve the configuration of a sensitive benzylic stereocenter.
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