Formal total synthesis of the polyketide macrolactone narbonolide.
[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.
Venkatraman
Lakshmanan
L
Department of Medicinal Chemistry, 308 Harvard Street S.E., 8-101 WDH, University of Minnesota, Minneapolis, Minnesota 55455-0353, USA.
Aldrich
Courtney C
CC
Sherman
David H
DH
Fecik
Robert A
RA
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D007783:Lactones; D018942:Macrolides