An efficient synthesis of 3-hetero-13,14-dihydro prostaglandin F1alpha analogues

Org Lett. 2001 Mar 8;3(5):791-4. doi: 10.1021/ol015613a.

Abstract

[structure: see text]. A new class of 3-hetero-13,14-dihydro prostaglandin F(1)(alpha) analogues was synthesized from a common intermediate. The latter was constructed via a two-step, three-component process. The lower chain, containing the 15-(phenoxymethyl) group, was synthesized in enantiopure form using Jacobsen's (salen)Co-catalyzed kinetic resolution of a terminal epoxide with phenol.

MeSH terms

  • Animals
  • COS Cells
  • Glycine / chemistry
  • Indicators and Reagents
  • Prostaglandins F / chemical synthesis*
  • Prostaglandins F / metabolism
  • Prostaglandins F, Synthetic / chemical synthesis*
  • Prostaglandins F, Synthetic / metabolism
  • Receptors, Prostaglandin / metabolism
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Prostaglandins F
  • Prostaglandins F, Synthetic
  • Receptors, Prostaglandin
  • Glycine
  • prostaglandin F1