Stereoselective synthesis of scyphostatin hydrophilic moiety

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

Research output: Contribution to journalArticle

4 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

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Allylation
Glycols
Alkenes
Substrates
cyclohexanone
scyphostatin

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective synthesis of scyphostatin hydrophilic moiety. / Kuwata, Kazuaki; Suzuki, Masashi; Inami, Yoshikazu; Hanaya, Kengo; Sugai, Takeshi; Shoji, Mitsuru.

In: Tetrahedron Letters, Vol. 55, No. 17, 23.04.2014, p. 2856-2858.

Research output: Contribution to journalArticle

Kuwata, Kazuaki ; Suzuki, Masashi ; Inami, Yoshikazu ; Hanaya, Kengo ; Sugai, Takeshi ; Shoji, Mitsuru. / Stereoselective synthesis of scyphostatin hydrophilic moiety. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 17. pp. 2856-2858.
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AU - Sugai, Takeshi

AU - Shoji, Mitsuru

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