Formal Total Synthesis of the Polyketide Macrolactone Narbonolide

An improved synthesis of (3S)-3-dihydronarbonolide is reported that constitutes a formal total synthesis of the 14-membered macrolactone antibiotic narbonolide. The key step was an intramolecular Nozaki−Hiyama−Kishi coupling to accomplish macrocyclization in improved yield. The high level of converg...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-09, Vol.70 (18), p.7267-7272
Main Authors: Venkatraman, Lakshmanan, Aldrich, Courtney C, Sherman, David H, Fecik, Robert A
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lactones - chemical synthesis
Macrolides - chemical synthesis
Organic chemistry
Preparations and properties
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Summary:An improved synthesis of (3S)-3-dihydronarbonolide is reported that constitutes a formal total synthesis of the 14-membered macrolactone antibiotic narbonolide. The key step was an intramolecular Nozaki−Hiyama−Kishi coupling to accomplish macrocyclization in improved yield. The high level of convergence will also allow us to rapidly synthesize narbonolide analogues for the study of enzymes in the pikromycin biosynthetic pathway.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050924a