Synthesis of a C4-epi-C1-C6 fragment of FR901464 using a novel bromolactolization

Org Lett. 2004 Oct 14;6(21):3655-8. doi: 10.1021/ol049160w.

Abstract

[reaction: see text] A synthesis of a C4-epi-C1-C6 fragment of the antitumor agent FR901464 is reported. The advanced intermediate prepared in this study contains two of the three correct stereocenters found in the C1-C6 moiety of FR901464. For the preparation of this intermediate, we have developed a highly diastereoselective bromolactolization of a delta-alkenyl ketone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Bromine / chemistry*
  • Lactones / chemistry*
  • Pyrans / chemical synthesis
  • Spiro Compounds / chemical synthesis

Substances

  • Antineoplastic Agents
  • FR 901464
  • Lactones
  • Pyrans
  • Spiro Compounds
  • Bromine