Enantioselective Synthesis and Absolute Configuration Assignment of Gabosine O. Synthesis of (+)- and (−)-Gabosine N and (+)- and (−)-Epigabosines N and O

A rational approach to the synthesis of gabosines and other related carba-sugars starting from a masked p-benzoquinone has been designed. The enantioselective acetylation of the hydroxyketal 2 provides a practical entry to either enantiomer of the target products. The strategy has been applied to th...

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Bibliographic Details
Published in:Organic letters 2006-04, Vol.8 (8), p.1617-1620
Main Authors: Alibés, Ramón, Bayón, Pau, de March, Pedro, Figueredo, Marta, Font, Josep, Marjanet, Georgina
Format: Article
Language:English
Subjects:
Benzoquinones - chemical synthesis
Benzoquinones - chemistry
Catalysis
Cyclohexanones
Molecular Structure
Stereoisomerism
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Summary:A rational approach to the synthesis of gabosines and other related carba-sugars starting from a masked p-benzoquinone has been designed. The enantioselective acetylation of the hydroxyketal 2 provides a practical entry to either enantiomer of the target products. The strategy has been applied to the synthesis of (+)- and (−)-gabosines N and O and (+)- and (−)-epigabosines N and O. The absolute configuration of natural gabosine O has been established.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol060173e