Expedient construction of the Ziegler intermediate useful for the synthesis of forskolin via consecutive rearrangements

Org Lett. 2009 Dec 3;11(23):5442-4. doi: 10.1021/ol902133q.

Abstract

The Ziegler intermediate, useful for the total synthesis of forskolin, was synthesized in 10 reaction steps starting from commercially available alpha-ionone. This highly efficient synthesis relies on the success of two consecutive highly regio- and stereoselective rearrangements. The current synthesis has not only established an efficient synthetic route to access the Ziegler intermediate but it has also paved a way to the structural optimization of forskolin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coleus / chemistry
  • Colforsin / chemical synthesis*
  • Colforsin / chemistry
  • Cyclization
  • Molecular Structure
  • Norisoprenoids / chemistry*
  • Stereoisomerism

Substances

  • Norisoprenoids
  • Colforsin
  • alpha-ionone