陶霉素A大环：不对称全合成及相对立体化学的修正

The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry.

作者信息

deGruyter Justine N, Maio William A

机构信息

Department of Chemistry and Biochemistry, New Mexico State University , Las Cruces, New Mexico 88003, United States.

出版信息

Org Lett. 2014 Oct 3;16(19):5196-9. doi: 10.1021/ol5025585. Epub 2014 Sep 23.

DOI:10.1021/ol5025585

PMID:25248034

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4184443/

Abstract

The first asymmetric total synthesis and revision of the relative configuration of the 12-membered taumycin A macrocycle is described. Key to the success of this work was a novel α-keto ketene macrocyclization that provided an efficient means by which to access two diastereomers of the desired macrolide without the need to employ additional coupling agents or unnecessary oxidation state adjustments.

摘要

本文描述了12元大环内酯类抗生素陶霉素A的首次不对称全合成以及其相对构型的修正。这项工作成功的关键在于一种新型的α-酮烯酮大环化反应，该反应提供了一种有效的方法，无需使用额外的偶联剂或进行不必要的氧化态调整，即可获得所需大环内酯的两种非对映异构体。