Light-mediated total synthesis of 17-deoxyprovidencin

Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3859-62. doi: 10.1002/anie.201400617. Epub 2014 Mar 6.

Abstract

An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photochemical E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring.

Keywords: furanocembranoids; macrocycles; metathesis; photoisomerization; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism

Substances

  • Diterpenes
  • providencin