Total Synthesis of (-)-Batrachotoxinin A: A Local-Desymmetrization Approach

J Am Chem Soc. 2020 Feb 26;142(8):3675-3679. doi: 10.1021/jacs.9b12882. Epub 2020 Feb 14.

Abstract

An enantioselective total synthesis of (-)-batrachotoxinin A is accomplished based on a key photoredox coupling reaction and the subsequent local-desymmetrization operation. After the expedient assembly of the highly oxidized steroid skeleton, a delicate sequence of redox manipulations was carried out to deliver a late-stage intermediate on gram scale-and ultimately (-)-batrachotoxinin A in an efficient manner.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Batrachotoxins / chemical synthesis*
  • Batrachotoxins / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Batrachotoxins