Intramolecular direct Aldol reactions of sugar diketones: Syntheses of valiolamine and validoxylamine G

Tony K.M. Shing; Hau M. Cheng

doi:10.1021/ol801889n

Intramolecular direct Aldol reactions of sugar diketones: Syntheses of valiolamine and validoxylamine G

Tony K.M. Shing, Hau M. Cheng

Department of Chemistry

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

29 Citations (Scopus)

Abstract

(Chemical Equation Presented) A new and stereoselective intramolecular direct aldol reaction of diketones derived from carbohydrates has been developed to construct carbocycles with D-gluco-, D-galacto, D-manno-, and L-ido-configurations. The stereochemical outcome of the aldol reaction of the diketone is dependent on the base used. Transformation of D-gluco-aldols readily affords valiolamine which also constitutes a formal synthesis of voglibose. Facile conversion of D-gluco-cyclohexanones into validoxylamine G has been achieved in 12 steps with 15.1% overall yield from D-glucose.

Original language	English
Pages (from-to)	4137-4139
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	18
DOIs	https://doi.org/10.1021/ol801889n
Publication status	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol801889n

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abstract = "(Chemical Equation Presented) A new and stereoselective intramolecular direct aldol reaction of diketones derived from carbohydrates has been developed to construct carbocycles with D-gluco-, D-galacto, D-manno-, and L-ido-configurations. The stereochemical outcome of the aldol reaction of the diketone is dependent on the base used. Transformation of D-gluco-aldols readily affords valiolamine which also constitutes a formal synthesis of voglibose. Facile conversion of D-gluco-cyclohexanones into validoxylamine G has been achieved in 12 steps with 15.1% overall yield from D-glucose.",

author = "Shing, {Tony K.M.} and Cheng, {Hau M.}",

year = "2008",

doi = "10.1021/ol801889n",

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N2 - (Chemical Equation Presented) A new and stereoselective intramolecular direct aldol reaction of diketones derived from carbohydrates has been developed to construct carbocycles with D-gluco-, D-galacto, D-manno-, and L-ido-configurations. The stereochemical outcome of the aldol reaction of the diketone is dependent on the base used. Transformation of D-gluco-aldols readily affords valiolamine which also constitutes a formal synthesis of voglibose. Facile conversion of D-gluco-cyclohexanones into validoxylamine G has been achieved in 12 steps with 15.1% overall yield from D-glucose.

AB - (Chemical Equation Presented) A new and stereoselective intramolecular direct aldol reaction of diketones derived from carbohydrates has been developed to construct carbocycles with D-gluco-, D-galacto, D-manno-, and L-ido-configurations. The stereochemical outcome of the aldol reaction of the diketone is dependent on the base used. Transformation of D-gluco-aldols readily affords valiolamine which also constitutes a formal synthesis of voglibose. Facile conversion of D-gluco-cyclohexanones into validoxylamine G has been achieved in 12 steps with 15.1% overall yield from D-glucose.

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Intramolecular direct Aldol reactions of sugar diketones: Syntheses of valiolamine and validoxylamine G

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