甲氧基福米霉素的 1,2-加成到酮亚胺的合成。

Synthesis of methoxyfumimycin with 1,2-addition to ketimines.

机构信息

Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany.

出版信息

J Org Chem. 2010 Jan 1;75(1):229-32. doi: 10.1021/jo902026s.

DOI:10.1021/jo902026s

PMID:19957921

Abstract

The synthesis of (+/-)-methoxyfumimycin, a potential new bacterial peptide deformylase (PDF) inhibitor, is reported. To generate the stereogenic fully substituted carbon, the key step is a 1,2-addition of a methyl Grignard reagent to a ketimine. The overall synthetic strategy involves a Dakin oxidation of a vanillin derivative, Friedel-Crafts acylation, Claisen rearrangement, lactonization, and rhodium-catalyzed olefin isomerization.

摘要

报告了 (+/-)-甲氧基福米霉素的合成，这是一种有潜力的新型细菌肽脱甲酰基酶（PDF）抑制剂。为了生成具有立体化学完全取代的碳，关键步骤是甲基格氏试剂向酮亚胺的 1,2-加成。总体合成策略涉及香草醛衍生物的 Dakin 氧化、Friedel-Crafts 酰化、Claisen 重排、内酯化和铑催化的烯烃异构化。