A new synthesis of key intermediates for the assembly of polycyclic ethers: Yb(OTf)3-promoted formation of O,S-acetals from α- fluorosulfides and alcohols

Masayuki Inoue, Shuji Yamashita, Masahiro Hirama

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

We report a new reaction for the direct construction of O,S-acetals, key intermediates in the assembly of fused polycyclic ethers. α- Fluorosulfides and secondary alcohols were coupled by the action of Yb(OTf) 3 to generate O,S-acetals in high yield. The neutral and selective nature of the reaction should be useful for synthesizing natural and artificial polyethers with multisensitive functionalities.

Original languageEnglish
Pages (from-to)2053-2056
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number10
DOIs
Publication statusPublished - 2004 Mar 1

Keywords

  • Ciguatoxin
  • Convergent synthesis
  • Nucleophilic addition
  • O,S-Acetal
  • Polyether
  • α-Fluorosulfide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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