Stereocontrolled synthesis of lankanolide from 1,6-anhydro-beta-D-glucopyranose (levoglucosan): 1, synthesis of the C-1/7 and C-8/15 segments

Stereocontrolled synthesis of lankanolide from 1,6-anhydro-beta-D-glucopyranose (levoglucosan): 1, synthesis of the C-1/7 and C-8/15 segments

A scheme has been designed for the stereocontrolled synthesis of lankanolide, the aglycon of lankamycin. Synthesis of its C-1/7 and C-8/15 segments has been accomplished starting from 1,6-anhydro-2,4-dideoxy-2,4-di-C-methyl-beta-D-glucopyranose.

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Bibliographic Details
Published in:Carbohydrate research Vol. 200; p. 209
Main Authors: Kochetkov, N K, Yashunsky, D V, Sviridov, A F, Ermolenko, M S
Format: Journal Article
Language:English
Published: Netherlands 25-04-1990
Subjects:
Anti-Bacterial Agents - chemical synthesis
Chemical Phenomena
Chemistry
Lactones - chemical synthesis
Macrolides
Stereoisomerism
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Description
Summary:A scheme has been designed for the stereocontrolled synthesis of lankanolide, the aglycon of lankamycin. Synthesis of its C-1/7 and C-8/15 segments has been accomplished starting from 1,6-anhydro-2,4-dideoxy-2,4-di-C-methyl-beta-D-glucopyranose.
ISSN:0008-6215
DOI:10.1016/0008-6215(90)84192-W