Original scientific paper

Synthesis of Macrolide Antibiotics. IV. Stereoselective Syntheses of the 3-O-Methyl and the 11-O-Methyl Derivatives of the C(1)-C(6) Segment of Erythronolides A and B and the C(9)-C(15) Segment of Erythronolide A, Respectively

Momčilo Miljković ; Department of Biological Chemistry, The Milton S. Hershey Medical Center The Pennsylvania State University, Hershey, Pennsylvania 17033
T. C. Choong ; Department of Biological Chemistry, The Milton S. Hershey Medical Center The Pennsylvania State University, Hershey, Pennsylvania 17033
Dj. Glišin ; Department of Biological Chemistry, The Milton S. Hershey Medical Center The Pennsylvania State University, Hershey, Pennsylvania 17033

Abstract

By appropriate dissection of the macrocyclic lactone ring of
methymycin erythromycins A and B, picromycin and narbomycin,
carbohydrate-like structural segments were obtained. The finding
that the anomeric configuration of a glycopyranoside effectively
controls the stereochemistry of various addition reactions to sp'
(C=O and C=C) carbon atoms of a glycopranoside ring led to the
development of a general stereoselective approach for the synthesis
of the chiral carbon framework of the polyoxomacrolide aglycones of methymycin, erythromycin A and B, picromycin and narbomycin. Stereoselective synthesis of methyl 2,4,7-trideoxy-2-C, 3-0, 4-C-tri-methyl-~-L-ido-heptopyranosid-6-ulose and methyl 2,6,7-trideoxy-2-C, 3-0, 4-C-trimethyl-a-D-glucoheptopyranoside, representing the 3-0-methyl and the 11-0-methyl derivatives of the C(1)-C(6) segment of erythronolides A and B and the C(9)-C(15) segment of erythronolide A, respectively, is described.

Keywords

Hrčak ID:

178055

URI

https://hrcak.srce.hr/178055

Publication date:

6.3.1986.

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