Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: a formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

Org Biomol Chem. 2013 Feb 28;11(8):1280-5. doi: 10.1039/c3ob27321k.

Abstract

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(III)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / chemistry*
  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry
  • Catalysis
  • Epoxy Compounds / chemistry*
  • Esters / chemistry*
  • Hydrolysis
  • Kinetics
  • Molecular Structure
  • Optical Phenomena
  • Organometallic Compounds / chemistry
  • Paroxetine / chemical synthesis*
  • Paroxetine / chemistry
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Stereoisomerism

Substances

  • 6-methyl-4,4,5-trifluorohept-1,5-dien-3-ol
  • Alkadienes
  • Epoxy Compounds
  • Esters
  • Organometallic Compounds
  • Piperidines
  • Ro 67-8867
  • Paroxetine
  • 4-Butyrolactone