A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides by sulfoxide-metal exchange as the key reaction and an application to a total synthesis of male bean weevil sex attractant

Tsuyoshi Satoh, Noriko Hanaki, Yuko Kuramochi, Yujiro Inoue, Kayo Hosoya, Ken Sakai

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53 Citations (Scopus)

Abstract

The sulfoxide-metal exchange reaction of β-acetoxy sulfoxides or β-mesyloxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with a Grignard reagent or alkyllithium at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-substituted ethenyl p-tolyl sulfoxides. A synthesis of (-)-methyl (E)-2,4,5-tetradecatrienoate, a male bean weevil sex attractant, was realized by this method.

Original languageEnglish
Pages (from-to)2533-2549
Number of pages17
JournalTetrahedron
Volume58
Issue number13
DOIs
Publication statusPublished - Mar 25 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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