Highly Stereoselective 1,4-Addition of the Enolate Generated from 6-Deoxy-D-Glucopyranoside-Derived Propionyl Ester to Methyl Crotonate: Application to Total Synthesis of (-)-Lasiol

Shingo Asano, Tetsuo Tamai, Kiichiro Totani, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

1,4-Addition of the enolate generated from methyl 6-deoxy-2,3-di-O-(t- butyldimethylsilyl)-4-O-propionyl-α-D-glucopyranoside to methyl crotonate provided a single anti-adduct with exceptionally high stereoselectivity. From this adduct, (-)-lasiol, an acyclic monoterpene alcohol isolated from the males of Lasius meridionalis ants, was synthesized concisely.

Original languageEnglish
Pages (from-to)2252-2254
Number of pages3
JournalSynlett
Issue number14
DOIs
Publication statusPublished - 2003 Jan 1

    Fingerprint

Keywords

  • (-)-lasiol
  • 1,4-addition
  • Asymmetric synthesis
  • Chiral auxiliary
  • D-glucose

ASJC Scopus subject areas

  • Organic Chemistry

Cite this