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

化学科

研究成果: Article › 査読

20 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	6001-6005
ページ数	5
ジャーナル	Tetrahedron
巻	67
号	33
DOI	https://doi.org/10.1016/j.tet.2011.06.028
出版ステータス	Published - 2011 8月 19

ASJC Scopus subject areas

生化学
創薬
有機化学

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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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SN - 0040-4020

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

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