Synthesis of A B C-ring subunit of C-nor-D-homo-steroidal alkaloids: towards the total synthesis of cyclopamine

Chin J Nat Med. 2013 May;11(3):277-83. doi: 10.1016/S1875-5364(13)60029-1.

Abstract

A practical approach to the synthesis of the A, B and C-ring subunit of cyclopamine has been developed. This synthetic tactic highlights the utility of mandelate acetal-mediated resolution of the fused ring ketone (±)-4 and IBX-mediated oxidation cascades from 12 to 9. The availability of advanced intermediates from enantiomerically pure (+)-4 and 2 could provide efficient access to biologically active and structurally diverse C-nor-D-homo-steroidal alkaloids such as cyclopamine.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic / methods*
  • Molecular Structure
  • Organic Chemistry Phenomena
  • Stereoisomerism
  • Steroids / chemistry
  • Veratrum Alkaloids / chemical synthesis*
  • Veratrum Alkaloids / chemistry

Substances

  • Steroids
  • Veratrum Alkaloids
  • cyclopamine