Stereoselective synthesis of the cytotoxic macrolide FD-891

Org Lett. 2006 Jun 22;8(13):2695-8. doi: 10.1021/ol060669w.

Abstract

[reaction: see text] A total synthesis of the naturally occurring, cytotoxic macrolide FD-891 is described. Three fragments were first stereoselectively constructed using mainly asymmetric aldol and allylation reactions. The complete framework was then assembled using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Macrolides / chemical synthesis*
  • Macrolides / pharmacology
  • Molecular Structure
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Macrolides
  • FD 891