A --> J prostaglandin swap: a new tactic for cyclopentenone prostaglandin synthesis

J Org Chem. 2003 Aug 22;68(17):6803-5. doi: 10.1021/jo034501p.

Abstract

A practical methodology for the synthesis of J-type prostaglandins has been developed starting from the well-consolidated approaches established for the synthesis of A-type prostaglandins. An efficient 1,3-allylic transposition of the C-9 hydroxyl group of intermediate 4 furnished the advanced precursor 5 for J(2) synthesis. Our optimized A-J swap protocol employed selenium chemistry, involving the [2,3] sigmatropic rearrangement of secondary allylic selenoxide 11a.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Indicators and Reagents
  • Models, Molecular
  • Prostaglandin D2 / analogs & derivatives*
  • Prostaglandin D2 / chemistry*
  • Prostaglandins / chemical synthesis
  • Prostaglandins / chemistry*
  • Prostaglandins A / chemistry*

Substances

  • Indicators and Reagents
  • Prostaglandins
  • Prostaglandins A
  • 9-deoxy-delta-9-prostaglandin D2
  • Prostaglandin D2