Enantioselective total synthesis of borrelidin

J Am Chem Soc. 2003 Feb 12;125(6):1458-9. doi: 10.1021/ja028941u.

Abstract

The first total synthesis of the natural product borrelidin is described. The propionate fragment of the molecule was concisely synthesized through catalytic enantioselective reductive aldol reactions, a catalytic Negishi coupling, and a catalytic directed hydrogenation. The propionate segment was then fused to the vinyl iodide fragment through a catalytic Sonogashira coupling. Subsequent catalytic hydrostannylation and catalytic cyanation allowed access to the target structure.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemical synthesis
  • Fatty Alcohols / chemical synthesis*
  • Stereoisomerism
  • Streptomyces / chemistry

Substances

  • Angiogenesis Inhibitors
  • Enzyme Inhibitors
  • Fatty Alcohols
  • borrelidin