A Concise Total Synthesis of Tryprostatins A and B and Epimers

IF 4.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ACS Omega Pub Date : 2025-10-08 DOI:10.1021/acsomega.5c07992

Sophia Seideman, , , Khorshada Jahan, , , Frank Holger Foersterling, , and , M. Mahmun Hossain*,

引用次数: 0

Abstract

A concise four-step total synthesis of tryprostatins A and B has been developed, starting from commercially available gramine. The key step features a coupling between a C2,N′-diprenylated gramine salt and a diketopiperazine mediated by quinine as a bifunctional base. The synthesis afforded tryprostatins A and B along with their respective epimers in 1:1 ratios as determined by isolation and separation via column chromatography. The overall combined yields were 22% for tryprostatin A and its epimer and 44% for tryprostatin B and its epimer.

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Tryprostatins A、B及引物的简明全合成

一个简洁的四步全合成tryprostatins A和B已经开发，从商业上可获得的谷氨酰胺开始。关键步骤是C2，N ' -二丙烯化谷氨酰胺盐和奎宁作为双功能碱介导的二酮哌嗪之间的偶联。通过柱层析分离和分离，以1:1的比例合成了tryprostatins A和B及其各自的外显体。总产率为22%，总产率为44%。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Omega Chemical Engineering-General Chemical Engineering

CiteScore

6.60

自引率

4.90%

发文量

3945

审稿时长

2.4 months

期刊介绍： ACS Omega is an open-access global publication for scientific articles that describe new findings in chemistry and interfacing areas of science, without any perceived evaluation of immediate impact.