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 journalArticle

27 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 languageEnglish
Pages (from-to)5150-5153
Number of pages4
JournalOrganic Letters
Volume12
Issue number22
DOIs
Publication statusPublished - 2010 Nov 19
Externally publishedYes

Fingerprint

Glycosylation
carbohydrates
routes
analogs
synthesis
Macrolides
Carbohydrates
methymycin

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

A de novo approach to the synthesis of glycosylated methymycin analogues with structural and stereochemical diversity. / Borisova, Svetlana A.; Guppi, Sanjeeva R.; Kim, Hak Joong; Wu, Bulan; Penn, John H.; Liu, Hung Wen; O'Doherty, George A.

In: Organic Letters, Vol. 12, No. 22, 19.11.2010, p. 5150-5153.

Research output: Contribution to journalArticle

Borisova, Svetlana A. ; Guppi, Sanjeeva R. ; Kim, Hak Joong ; Wu, Bulan ; Penn, John H. ; Liu, Hung Wen ; O'Doherty, George A. / A de novo approach to the synthesis of glycosylated methymycin analogues with structural and stereochemical diversity. In: Organic Letters. 2010 ; Vol. 12, No. 22. pp. 5150-5153.
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