A concise total synthesis of (-)-maoecrystal Z

J Am Chem Soc. 2011 Sep 28;133(38):14964-7. doi: 10.1021/ja2073356. Epub 2011 Aug 30.

Abstract

The first total synthesis of (-)-maoecrystal Z is described. The key steps of the synthesis include a diastereoselective Ti(III)-mediated reductive epoxide coupling reaction and a diastereoselective Sm(II)-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (-)-maoecrystal Z in only 12 steps from (-)-γ-cyclogeraniol.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Diterpenes, Kaurane / chemical synthesis*
  • Diterpenes, Kaurane / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Diterpenes, Kaurane
  • maoecrystal Z