Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 1. Racemic and asymmetric synthesis of bicyclo[4.3.1] key building blocks

J Am Chem Soc. 2002 Mar 13;124(10):2183-9. doi: 10.1021/ja012010l.

Abstract

A brief introduction into the chemistry of the CP-molecules is followed by first-generation synthetic sequences toward key building blocks for their total synthesis. Processes for both racemic and enantiomerically enriched bicyclo[4.3.1] ketone 6 or its equivalent are described, and the absolute stereochemistries of the optically enriched intermediates are determined. The efficient route developed to racemic 6 and the ready access to both enantiomers of key building blocks provided the opportunity for the total synthesis of the CP-molecules and determination of their absolute stereochemistry.

Publication types

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

MeSH terms

  • Enzyme Inhibitors / chemical synthesis*
  • Maleic Anhydrides / chemical synthesis*
  • Stereoisomerism

Substances

  • CP 225917
  • CP 263114
  • Enzyme Inhibitors
  • Maleic Anhydrides