A convenient entry to C2- and C3-substituted gulono-gamma-lactone derivatives from L-ascorbic acid

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Authors
Olabisi, Ayodele O.
Mahindaratne, Mathew P. D.
Wimalasena, Kandatege
Advisors
Issue Date
2005-08-19
Type
Article
Keywords
Research Support, N.I.H., Extramural
Research Projects
Organizational Units
Journal Issue
Citation
The Journal of organic chemistry. 2005 Aug 19; 70(17): 6782-9.
Abstract

A convenient method to obtain unknown chiral C2- and C3-functionalized aldono-1,4-lactone derivatives starting from l-ascorbic acid, which would be valuable in the synthesis of derivatives of various pharmacologically active agents for structure-activity studies, is described. The practicality of this approach is demonstrated by the synthesis of a series of 5,6-O-isopropylidene-2-allyl-3-keto-l-galactono-gamma-lactone and 5,6-O-isopropylidene-3-allyl-2-keto-l-galactono-gamma-lactone derivatives using the thermal Claisen rearrangement of the corresponding 3-O- and 2-O-allyl derivatives of 5,6-O-isopropylidene-l-ascorbic acid, respectively, followed by stereospecific reduction to the corresponding alcohols. The synthetic steps are shown to be efficient, and enantiospecific, and they proceed with high yields.

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Publisher
American Chemical Society
Journal
Book Title
Series
The Journal of organic chemistry
J. Org. Chem.
PubMed ID
DOI
ISSN
0022-3263
EISSN