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

Tony K.M. Shing; Hau M. Cheng

doi:10.1021/jo0709697

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

Tony K.M. Shing, Hau M. Cheng

Research output: Contribution to journal › Article › peer-review

49 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 language	English
Pages (from-to)	6610-6613
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	17
DOIs	https://doi.org/10.1021/jo0709697
Publication status	Published - 2007 Aug 17
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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).",

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AU - Cheng, Hau M.

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AB - (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).

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

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