Synthesis of Luffarin L and 16-epi-Luffarin L Using a Temporary Silicon-Tethered Ring-Closing Metathesis Reaction

J Org Chem. 2015 Jun 19;80(12):6447-55. doi: 10.1021/acs.joc.5b00876. Epub 2015 May 29.

Abstract

The first synthesis of luffarin L (1) and 16-epi-luffarin L (2) by a silicon-tethered ring closing metathesis as a key step has been achieved. The stereochemistry and absolute configuration of the natural sesterterpenolide luffarin L (1) and a new route for the stereoselective synthesis of sesterterpenolides with a luffarane skeleton have been established.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Molecular Structure
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Silicon / chemistry*
  • Stereoisomerism

Substances

  • Sesquiterpenes
  • luffarin L
  • Silicon