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Updated: Aug 16, 2026

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028
Published on: January 13, 2017
Formal total synthesis of the polyketide macrolactone narbonolide
Lakshmanan Venkatraman1, Courtney C Aldrich, David H Sherman
1Department of Medicinal Chemistry, 308 Harvard Street S.E., 8-101 WDH, University of Minnesota, Minneapolis, Minnesota 55455-0353, USA.
Abstract:
[reaction: see text] 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.
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