Total synthesis of (±)-przewalskin B

J Org Chem. 2014 Mar 21;79(6):2746-50. doi: 10.1021/jo500047q. Epub 2014 Mar 10.

Abstract

A concise total synthesis of przewalskin B was accomplished from readily available diene 7. Key features of the synthesis involved a Diels-Alder reaction to install the A ring, a Claisen-Johnson rearrangement to establish the spiro-quaternary center, and a ring-closing metathesis (RCM) of a sterically crowded system to construct the cyclic enone moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cycloaddition Reaction
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Stereoisomerism

Substances

  • Diterpenes
  • Przewalskin B