Synthetic studies on amphidinolide B1

Org Lett. 2006 Feb 2;8(3):427-30. doi: 10.1021/ol052620g.

Abstract

[structure: see text]. The syntheses of three fragments, 2, 3, and 4, of amphidinolide B1 have been accomplished. The 1,3-isomerization of allylic alcohol 10 was accomplished via rhenium oxo catalysis and has been applied successfully in the synthesis. (-)-MIB-catalyzed asymmetric vinylzinc addition to aldehyde 31 and the regio- and stereoselective epoxidation of unsymmetrical divinyl methanol 32 were key steps.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Catalysis
  • Dinoflagellida / chemistry
  • Indicators and Reagents
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Macrolides
  • amphidinolide B1