Ring-closing metathesis (RCM) based synthesis of the macrolactone core of amphidinolactone A

Org Biomol Chem. 2011 Aug 21;9(16):5630-2. doi: 10.1039/c1ob05335c. Epub 2011 May 26.

Abstract

A convergent synthesis of the macrolactone core of amphidinolactone A has been achieved, in a 10 step linear sequence with 32% overall yield, through a ring-closing metathesis reaction as the macrolactonization step. The RCM precursor was obtained by the union of acid and alcohol fragments derived from (R)-epichlorohydrin and (R)-2,3-O-isopropylidene glyceraldehyde, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cytotoxins / chemical synthesis
  • Dinoflagellida / chemistry*
  • Macrolides / chemical synthesis*
  • Models, Molecular

Substances

  • Cytotoxins
  • Macrolides
  • amphidinolactone A