Stereoselective synthesis of scyphostatin hydrophilic moiety

Kazuaki Kuwata, Masashi Suzuki, Yoshikazu Inami, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A stereoselective synthesis of scyphostatin hydrophilic moiety was accomplished. Substrate- and reagent-controlled dihydroxylation of tri- and monosubstituted alkenes afforded desired diols, respectively. Chemo- and stereoselective allylation of α-(methoxycarbonyl)cyclohexanone provided allylcyclohexanol. Oxidative cleavage of glycol and subsequent β-elimination of siloxycyclohexanone furnished the desired epoxycyclohexenone.

Original languageEnglish
Pages (from-to)2856-2858
Number of pages3
JournalTetrahedron Letters
Volume55
Issue number17
DOIs
Publication statusPublished - 2014 Apr 23

Keywords

  • Epoxycyclohexenone
  • Hydrophilic moiety
  • Scyphostatin
  • Stereoselective allylation
  • Stereoselective dihydroxylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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