Enantioselective total synthesis of (-)-laurenditerpenol

Org Lett. 2012 Sep 7;14(17):4666-9. doi: 10.1021/ol302106y. Epub 2012 Aug 20.

Abstract

A highly convergent total synthesis of (-)-laurenditerpenol has been accomplished through an organolithium to aldehyde nucleophilic addition. Preparation of the prerequisite key intermediates in optically pure form was based on an improved, short, and efficient synthesis of "wine lactone" from (S)-limonene and Corey's catalytic enantioselective Diels-Alder reaction of 2,5-dimethyl furan with diethyl fumarate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cyclohexenes / chemistry*
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Laurencia / chemistry
  • Limonene
  • Molecular Structure
  • Stereoisomerism
  • Terpenes / chemistry*

Substances

  • Cyclohexenes
  • Diterpenes
  • Terpenes
  • laurenditerpenol
  • Limonene