Enantioselective total synthesis of (-)-clavosolide B

Org Lett. 2007 Sep 27;9(20):3897-900. doi: 10.1021/ol7015115. Epub 2007 Sep 8.

Abstract

Enantioselective synthesis of 2, a revised structure for (-)-clavosolide B, was accomplished by a convergent approach, where syn-selective aldol, hydroxy-directed cyclopropanation, Mitsunobu inversion, Schmidt-type glycosylation, and macrolactonization reactions were utilized as key reactions. Comparison of 1H and 13C NMR spectra and optical rotation measurement confirmed the relative and absolute stereochemistry of clavosolide B (2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Imidoesters / chemistry
  • Ketones / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Molecular Structure
  • Porifera / chemistry
  • Stereoisomerism

Substances

  • Imidoesters
  • Ketones
  • Macrolides
  • clavosolide A
  • clavosolide B