Formal total synthesis of the polyketide macrolactone narbonolide

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

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

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 languageEnglish (US)
Pages (from-to)7267-7272
Number of pages6
JournalJournal of Organic Chemistry
Volume70
Issue number18
DOIs
StatePublished - Sep 2 2005

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