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Synthesis of several cleistrioside and cleistetroside natural products via a divergent de novo asymmetric approach.

ABSTRACT: The de novo asymmetric syntheses of several partially acylated dodecanyl tri- and tetra-rhamnoside natural products (cleistriosides-5 and 6 and cleistetrosides-2 to 7) have been achieved (19-24 steps). The divergent route requires the use of three or less protecting groups. The asymmetry was derived via Noyori reduction of an acylfuran. The rhamno-stereochemistry was installed by a diastereoselective palladium-catalyzed glycosylation, ketone reduction and dihydroxylation.

SUBMITTER: Wu B

PROVIDER: S-EPMC3059258 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Synthesis of several cleistrioside and cleistetroside natural products via a divergent de novo asymmetric approach.

Wu Bulan B Li Miaosheng M O'Doherty George A GA

Organic letters 20101101 23

The de novo asymmetric syntheses of several partially acylated dodecanyl tri- and tetra-rhamnoside natural products (cleistriosides-5 and 6 and cleistetrosides-2 to 7) have been achieved (19-24 steps). The divergent route requires the use of three or less protecting groups. The asymmetry was derived via Noyori reduction of an acylfuran. The rhamno-stereochemistry was installed by a diastereoselective palladium-catalyzed glycosylation, ketone reduction and dihydroxylation. ...[more]

PMID: 21038879

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