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

Svetlana A. Borisova; Sanjeeva R. Guppi; Hak Joong Kim; Bulan Wu; John H. Penn; Hung Wen Liu; George A. O'Doherty

doi:10.1021/ol102144g

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

Svetlana A. Borisova, Sanjeeva R. Guppi, Hak Joong Kim, Bulan Wu, John H. Penn, Hung Wen Liu, George A. O'Doherty

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

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 α/β- and d/l-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.

Original language	English
Pages (from-to)	5150-5153
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	22
DOIs	https://doi.org/10.1021/ol102144g
Publication status	Published - 2010 Nov 19
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol102144g

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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 α/β- and d/l-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.",

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AU - Borisova, Svetlana A.

AU - Guppi, Sanjeeva R.

AU - Kim, Hak Joong

AU - Wu, Bulan

AU - Penn, John H.

AU - Liu, Hung Wen

AU - O'Doherty, George A.

PY - 2010/11/19

Y1 - 2010/11/19

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AB - 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.

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

Abstract

ASJC Scopus subject areas

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