Asymmetric Total Synthesis of Amphirionin-2

J Org Chem. 2021 Aug 6;86(15):10006-10022. doi: 10.1021/acs.joc.1c00686. Epub 2021 Jul 16.

Abstract

A convergent route for the asymmetric total synthesis of potent anticancer polyketide natural product amphirionin-2 has been developed. Our initial synthetic trials revealed that the proposed structures of amphirionin-2 need to be revised consistent with a recent report of Fuwa et al., where the actual structure of amphirionin-2 was established. The key features of our synthesis comprised Sharpless asymmetric dihydroxylation, followed by cycloetherification, Wittig olefination, Julia-Kocienski olefination, and Crimmins propionate aldol reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Furans*
  • Molecular Structure
  • Polyketides*
  • Stereoisomerism

Substances

  • Furans
  • Polyketides
  • amphirionin-2