Synthesis of Rimocidinolide Methyl Ester, the Aglycone of (+)-Rimocidin

An efficient, convergent route based on cyanohydrin acetonide couplings was used for the synthesis of the aglycone of rimocidin, rimocidinolide methyl ester (1). Cyanohydrin acetonides were used as β‐hydroxyketone synthetic equivalents in the assembly of the polyol chain.

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-05, Vol.43 (21), p.2822-2826
Main Authors: Packard, Garrick K., Hu, Yueqing, Vescovi, Andrea, Rychnovsky, Scott D.
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Chromatography, Thin Layer
cyanohydrins
CC coupling
Indicators and Reagents
macrocycles
Macrolides - chemical synthesis
Magnetic Resonance Spectroscopy
natural products
Oxidation-Reduction
Polyenes - chemistry
Spectrophotometry, Infrared
Streptomyces - chemistry
total synthesis
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Description
Summary:An efficient, convergent route based on cyanohydrin acetonide couplings was used for the synthesis of the aglycone of rimocidin, rimocidinolide methyl ester (1). Cyanohydrin acetonides were used as β‐hydroxyketone synthetic equivalents in the assembly of the polyol chain.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200453697