A short andenantioselective total synthesis of two Cleistriosides and six Cleistetrosides aswell as two more to date unkown Cleistetrosides has been achieved. Thesynthesis is amenable to the installation of all the sugar carbons for these biologicallyactive natural products from commercially available achiral acetylfuan. Thesugar absolute stereochemistry was installed by means of a highlyenantioselective Noyori reduction and the anomeric stereochemistry by apalladium catalyzed glycosylation. The remaining rhamo-stereochemistrywas installed by highly disastereoselective post-glycosylation ketone reductionand alkene dihydroxylation. The route to the tetrasaccharide is comparable interms of total steps to the previous approaches and is more amenable to thesynthesis of all members of this family of oligosaccharide natural products.

De novo asymmetric synthesis of several cleistriosides and cleistetrosides

240th National Meeting (2010)

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