Formal total synthesis of the polyketide macrolactone narbonolide

Lakshmanan Venkatraman; Courtney C. Aldrich; David H. Sherman; Robert A. Fecik

doi:10.1021/jo050924a

Formal total synthesis of the polyketide macrolactone narbonolide

Lakshmanan Venkatraman, Courtney C. Aldrich, David H. Sherman, Robert A. Fecik

Medicinal Chemistry

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Abstract

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.

Original language	English (US)
Pages (from-to)	7267-7272
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	70
Issue number	18
DOIs	https://doi.org/10.1021/jo050924a
State	Published - Sep 2 2005

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abstract = "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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AU - Venkatraman, Lakshmanan

AU - Aldrich, Courtney C.

AU - Sherman, David H.

AU - Fecik, Robert A.

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AB - 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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Formal total synthesis of the polyketide macrolactone narbonolide

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