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, Kenichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticle

14 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
Publication statusPublished - 2003

Fingerprint

Crotonates
Stereoselectivity
Monoterpenes
Esters
Alcohols
lasiol

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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. / Asano, Shingo; Tamai, Tetsuo; Totani, Kiichiro; Takao, Kenichi; Tadano, Kin Ichi.

In: Synlett, No. 14, 2003, p. 2252-2254.

Research output: Contribution to journalArticle

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