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Synthesis of SL0101 carbasugar analogues: carbasugars via Pd-catalyzed cyclitolization and post-cyclitolization transformations.

ABSTRACT: A general approach to the stereoselective synthesis of 5a-carbasugars has been developed. The route mimics our palladium-catalyzed glycosylation/postglycosylation approach to carbohydrates in that it also utilizes a highly regio- and stereospecific palladium-catalyzed allylation and postglycosylation reaction sequence for the installation of either D- or L-cyclitols. This cyclitolization/postcyclitolization sequence was used for the enantioselective synthesis of a cyclitol analogue of SL0101, its D-sugar enantiomer, as well as several acetylation pattern analogues.

SUBMITTER: Shan M

PROVIDER: S-EPMC2892554 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Synthesis of SL0101 carbasugar analogues: carbasugars via Pd-catalyzed cyclitolization and post-cyclitolization transformations.

Shan Mingde M O'Doherty George A GA

Organic letters 20100701 13

A general approach to the stereoselective synthesis of 5a-carbasugars has been developed. The route mimics our palladium-catalyzed glycosylation/postglycosylation approach to carbohydrates in that it also utilizes a highly regio- and stereospecific palladium-catalyzed allylation and postglycosylation reaction sequence for the installation of either D- or L-cyclitols. This cyclitolization/postcyclitolization sequence was used for the enantioselective synthesis of a cyclitol analogue of SL0101, it ...[more]

PMID: 20518547

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