Enantiodivergent Formal Synthesis of (+)- and (−)-Cyclophellitol from d-Xylose Based on the Latent Symmetry Concept

Formal synthesis of (+)- and (−)-cyclophellitol from d-xylose has been accomplished through utilization of the latent plane of chirality present in the starting carbohydrate. The synthetic pathway is suitable for preparation and biological evaluation of cyclophellitol analogues in both enantiomeric...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-01, Vol.70 (2), p.742-745
Main Authors: Kireev, Artem S, Breithaupt, August T, Collins, William, Nadein, Oleg N, Kornienko, Alexander
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Cyclohexanols - chemical synthesis
Cyclohexanols - chemistry
Exact sciences and technology
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
Xylose - chemistry
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Summary:Formal synthesis of (+)- and (−)-cyclophellitol from d-xylose has been accomplished through utilization of the latent plane of chirality present in the starting carbohydrate. The synthetic pathway is suitable for preparation and biological evaluation of cyclophellitol analogues in both enantiomeric series.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048459p