聚酮大环内酯那波内酯的形式全合成。

Formal total synthesis of the polyketide macrolactone narbonolide.

作者信息

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

机构信息

Department of Medicinal Chemistry, 308 Harvard Street S.E., 8-101 WDH, University of Minnesota, Minneapolis, Minnesota 55455-0353, USA.

出版信息

J Org Chem. 2005 Sep 2;70(18):7267-72. doi: 10.1021/jo050924a.

DOI:10.1021/jo050924a

PMID:16122247

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.

摘要

[反应：见正文] 报道了(3S)-3-二氢纳波内酯的一种改进合成方法，该方法构成了14元大环内酯抗生素纳波内酯的形式全合成。关键步骤是分子内的野依-日向-岸耦合反应，以提高产率实现大环化。这种高度的汇聚性也将使我们能够快速合成纳波内酯类似物，用于研究苦霉素生物合成途径中的酶。