Total Synthesis of the Labdane Diterpenes Galanal A and B from Geraniol

J Org Chem. 2017 Feb 3;82(3):1575-1583. doi: 10.1021/acs.joc.6b02766. Epub 2017 Jan 12.

Abstract

The first total synthesis of galanal A and B has been achieved from naturally occurring geraniol. Key steps in this synthesis are the use of a Lewis acid assisted chiral Brønsted acid (chiral LBA) mediated cationic polyene cyclization and a titanocene-mediated radical cyclization for the asymmetric assembly of the "AB" ring and the construction of the all-carbon quaternary center at the junction of the "BC" ring, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyclic Monoterpenes
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Terpenes / chemistry*

Substances

  • Acyclic Monoterpenes
  • Diterpenes
  • Terpenes
  • galanal A
  • galanal B
  • geraniol