A C–H Functionalization Strategy Enables an Enantioselective Formal Synthesis of (−)-Aflatoxin B2

Nicholas A. Falcone, Aaron T. Bosse, Hojoon Park, Jin Quan Yu, Huw M.L. Davies, Erik J. Sorensen

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)9393-9397
Number of pages5
JournalOrganic letters
Volume23
Issue number24
DOIs
StatePublished - Dec 17 2021

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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