Total synthesis of (-)-borrelidin

Org Lett. 2004 May 27;6(11):1865-7. doi: 10.1021/ol049356w.

Abstract

The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is SmI(2)-mediated intramolecular Reformatsky-type reaction for macrocyclization after esterification between two segments. The two key segments were synthesized through chelation-controlled carbotitanation, chelation-controlled hydrogenation, stereoselective Reformatsky reaction, and MgBr(2).Et(2)O-mediated chelation-controlled allylation. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry
  • Cyclization
  • Fatty Alcohols / chemical synthesis*
  • Fatty Alcohols / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Streptomyces / chemistry

Substances

  • Anti-Bacterial Agents
  • Antimalarials
  • Fatty Alcohols
  • borrelidin