Intramolecular direct Aldol reactions of sugar diketones

Syntheses of valiolamine and validoxylamine G

Tony Kung Ming Shing, Hau M. Cheng

Research output: Contribution to journalArticle

27 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 languageEnglish
Pages (from-to)4137-4139
Number of pages3
JournalOrganic Letters
Volume10
Issue number18
DOIs
Publication statusPublished - 2008 Dec 1
Externally publishedYes

Fingerprint

sugars
Sugars
carbohydrates
Cyclohexanones
synthesis
glucose
configurations
Carbohydrates
Glucose
3-hydroxybutanal
validoxylamine G
valiolamine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Intramolecular direct Aldol reactions of sugar diketones : Syntheses of valiolamine and validoxylamine G. / Shing, Tony Kung Ming; Cheng, Hau M.

In: Organic Letters, Vol. 10, No. 18, 01.12.2008, p. 4137-4139.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Cheng, Hau M. / Intramolecular direct Aldol reactions of sugar diketones : Syntheses of valiolamine and validoxylamine G. In: Organic Letters. 2008 ; Vol. 10, No. 18. pp. 4137-4139.
@article{658644f95ca34048a031151b744d7e09,
title = "Intramolecular direct Aldol reactions of sugar diketones: Syntheses of valiolamine and validoxylamine G",
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 Kung Ming} and Cheng, {Hau M.}",
year = "2008",
month = "12",
day = "1",
doi = "10.1021/ol801889n",
language = "English",
volume = "10",
pages = "4137--4139",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "18",

}

TY - JOUR

T1 - Intramolecular direct Aldol reactions of sugar diketones

T2 - Syntheses of valiolamine and validoxylamine G

AU - Shing, Tony Kung Ming

AU - Cheng, Hau M.

PY - 2008/12/1

Y1 - 2008/12/1

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.

UR - http://www.scopus.com/inward/record.url?scp=55949104124&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=55949104124&partnerID=8YFLogxK

U2 - 10.1021/ol801889n

DO - 10.1021/ol801889n

M3 - Article

VL - 10

SP - 4137

EP - 4139

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 18

ER -