Toward an analogue of the transition state of preD3-D3 isomerization: stereoselective synthesis of linearly fused 6-8-6 carbocyclic systems

Org Lett. 2002 May 16;4(10):1651-4. doi: 10.1021/ol025756c.

Abstract

[reaction: see text] A stereoselective synthesis of 6-8-6 fused carbocyclic systems based on enol alkylation, ketone allylation, RCM, and Heck cyclization was developed to obtain compounds with a carbon framework that mimics the putative transition structure of the isomerization of previtamin D3 to vitamin D3.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cholecalciferol / analogs & derivatives*
  • Cholecalciferol / chemistry*
  • Indicators and Reagents
  • Isomerism
  • Models, Molecular
  • Oxidation-Reduction
  • Polycyclic Aromatic Hydrocarbons / chemistry*
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Polycyclic Aromatic Hydrocarbons
  • Cholecalciferol
  • previtamin D(3)