New Stereodivergent Approach to 3-Amino-2,3,6-trideoxysugars. Enantioselective Synthesis of Daunosamine, Ristosamine, Acosamine, and Epi-daunosamine

An enantioselective preparation of the four diastereomeric 3-amino-2,3,6-trideoxy-hexoses, key components of anthracycline antibiotics, has been developed. Sharpless catalytic asymmetric epoxidation of the (2E)-2,5-hexadien-1-ol, regioselective ring opening with azide, followed by convenient functio...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 17; pp. 3001 - 3004
Main Authors Ginesta, Xavier, Pastó, Mireia, Pericàs, Miquel A, Riera, Antoni
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.08.2003
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Azides - chemistry
Carbohydrate Conformation
Chemistry
Chemistry, Organic
Hexosamines - chemical synthesis
Hexosamines - chemistry
Methylation
Ozone - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
TRANSFORMATION
2,3-EPOXY ALCOHOLS
BIOLOGICAL EVALUATION
ALPHA-AMINO-ACIDS
DAUNOMYCINONE
BENZOYL-L-DAUNOSAMINE
SUGARS
DERIVATIVES
EFFICIENT
STEREOSELECTIVE SYNTHESIS
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Summary:An enantioselective preparation of the four diastereomeric 3-amino-2,3,6-trideoxy-hexoses, key components of anthracycline antibiotics, has been developed. Sharpless catalytic asymmetric epoxidation of the (2E)-2,5-hexadien-1-ol, regioselective ring opening with azide, followed by convenient functional group transformations, afforded the key aldehydes cis- or trans-6 in any configuration. The diastereoselective addition of methylmetal reagents to these aldehydes followed by ozonolysis gives access in a completely stereocontrolled manner to the four isomeric trideoxyaminosugars.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol034843h