大环菌肽 B 立体异构体的合成与生物活性。

Synthesis and Bioactivity of a Macrocidin B Stereoisomer.

机构信息

Organic Chemistry Laboratory, University of Bayreuth, Universitätsstrasse 30, 95440 Bayreuth, Germany.

Department of Microbial Drugs, Helmholtz Centre for Infection Research GmbH, Inhoffenstrasse 7, 38124 Braunschweig, Germany.

出版信息

Org Lett. 2021 Nov 5;23(21):8273-8276. doi: 10.1021/acs.orglett.1c03013. Epub 2021 Oct 11.

DOI:10.1021/acs.orglett.1c03013

PMID:34633201

Abstract

A stereoisomer of macrocidin B, a presumed metabolite of the fungus , was synthesized in 18 steps and 2.7% yield from protected l-tyrosine that was -β-ketoacylated with a fully functionalized octanoyl Meldrum's acid. Dieckmann condensation gave a 3-acyltetramic acid, which was macrocyclized via Williamson etherification between the phenol and -bromohydrin termini. This macrocidin B stereoisomer showed a weaker herbicidal effect than macrocidin A and no similar inhibitory effect on biofilms of .

摘要

一种真菌假定代谢产物大环菌素 B 的立体异构体，由经全功能化辛酰基 Meldrum's 酸 -β-酮酰化保护的 l-酪氨酸经 18 步反应以 2.7%的收率合成。Dieckmann 缩合得到 3-酰基四氢酸，该酸通过酚和 -溴代缩水甘油末端之间的Williamson 醚化反应进行大环化。这种大环菌素 B 的立体异构体的除草效果比大环菌素 A 弱，对生物膜也没有类似的抑制作用。