Synthesis and structure revision of the C43-C67 part of amphidinol 3

Org Lett. 2013 Jun 7;15(11):2846-9. doi: 10.1021/ol401176a. Epub 2013 May 21.

Abstract

Stereoselective synthesis of the C43-C67 part of amphidinol 3 (AM3) and its C51-epimer was achieved starting from a common intermediate corresponding to the tetrahydropyran moiety of AM3, via asymmetric oxidations and Julia-Kocienski olefination. By comparing NMR data of the synthetic specimens with those of AM3, the absolute configuration at C51 of AM3 was revised from R to S.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis
  • Alkenes / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Pyrans
  • amphidinol 3