Total synthesis of (±)-sculponeatin N

Org Lett. 2014 Jan 3;16(1):216-9. doi: 10.1021/ol403208g. Epub 2013 Dec 2.

Abstract

The first total synthesis of the (±)-sculponeatin N (a 6,7-seco-ent-kaurane diterpenoid discovered by Sun and co-workers) has been achieved. The features include a regio- and stereoselective aldol reaction to form a lactone, an intramolecular Diels-Alder reaction to install B and C rings simultaneously, and a radical cyclization to forge the D ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Terpenes
  • sculponeatin N