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A de novo approach to the synthesis of glycosylated methymycin analogues with structural and stereochemical diversity.

ABSTRACT: A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of ?/?- and d/l-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.

SUBMITTER: Borisova SA 

PROVIDER: S-EPMC2980555 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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A de novo approach to the synthesis of glycosylated methymycin analogues with structural and stereochemical diversity.

Borisova Svetlana A SA   Guppi Sanjeeva R SR   Kim Hak Joong HJ   Wu Bulan B   Penn John H JH   Liu Hung-Wen HW   O'Doherty George A GA  

Organic letters 20101019 22

A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of α/β- and d/l-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion. ...[more]

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