Short syntheses of gabosine I and gabosine G from δ-D-gluconolactone

Tony Kung Ming Shing, Hau M. Cheng

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

(Chemical Equation Presented) A short synthesis of gabosine I (1) from δ-D-gluconolactone (3) in four steps, involving a one-pot TPAP oxidation-K2-CO3-mediated intramolecular Horner-Wadsworth-Emmons (HWE) olefination as the key step, is described. Regioselective acetylation of the primary alcohol in gabosine I (1) then furnished gabosine G (2).

Original languageEnglish
Pages (from-to)6610-6613
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number17
DOIs
Publication statusPublished - 2007 Aug 17
Externally publishedYes

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Acetylation
Alcohols
Oxidation
gabosine I
gabosine G
beta-glucono-1,5-lactone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Short syntheses of gabosine I and gabosine G from δ-D-gluconolactone. / Shing, Tony Kung Ming; Cheng, Hau M.

In: Journal of Organic Chemistry, Vol. 72, No. 17, 17.08.2007, p. 6610-6613.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Cheng, Hau M. / Short syntheses of gabosine I and gabosine G from δ-D-gluconolactone. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 17. pp. 6610-6613.
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