Enantioselective synthesis of indolizidine alkaloid trans-209D

J Org Chem. 2008 Nov 7;73(21):8661-4. doi: 10.1021/jo801645p. Epub 2008 Oct 8.

Abstract

(S)-N-Boc-baikiain, readily accessible from enantiomerically enriched 2,3-epoxy-5-hexen-1-ol 4 (prepared by Sharpless asymmetric epoxidation), was used as the starting material in the synthesis of indolizidine alkaloid trans-209D , which was obtained in 13 steps and 14% yield from 1 (5% from 4).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Formic Acid Esters
  • Indolizines / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Formic Acid Esters
  • Indolizines
  • indolizidine 209D
  • t-butyloxycarbonyl group