Carbocyclization of d-glucose: Syntheses of gabosine i and streptol

Tony K.M. Shing; Y. Chen; Wai Lung Ng

doi:10.1016/j.tet.2011.06.028

Carbocyclization of d-glucose: Syntheses of gabosine i and streptol

Tony K.M. Shing, Y. Chen, Wai Lung Ng

Department of Chemistry

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

20 Citations (Scopus)

Abstract

d-Glucose was differentially protected with a trans-diacetal at C-2,3, an ethoxymethyl ether at C-4, and a tert-butyldimethylsilyl ether at C-6, and then carbocyclized via a key Horner-Wadsworth-Emmons (HWE) olefination to give a versatile synthetic intermediate, enone 13, which was readily transformed into gabosine I and streptol.

Original language	English
Pages (from-to)	6001-6005
Number of pages	5
Journal	Tetrahedron
Volume	67
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2011.06.028
Publication status	Published - 2011 Aug 19

Keywords

Carbohydrate
Natural products
Synthesis
Wittig reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.06.028

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T2 - Syntheses of gabosine i and streptol

AU - Shing, Tony K.M.

AU - Chen, Y.

AU - Ng, Wai Lung

PY - 2011/8/19

Y1 - 2011/8/19

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AB - d-Glucose was differentially protected with a trans-diacetal at C-2,3, an ethoxymethyl ether at C-4, and a tert-butyldimethylsilyl ether at C-6, and then carbocyclized via a key Horner-Wadsworth-Emmons (HWE) olefination to give a versatile synthetic intermediate, enone 13, which was readily transformed into gabosine I and streptol.

KW - Carbohydrate

KW - Natural products

KW - Synthesis

KW - Wittig reaction

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JO - Tetrahedron

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Carbocyclization of d-glucose: Syntheses of gabosine i and streptol

Abstract

Keywords

ASJC Scopus subject areas

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