Environment-friendly Simple, and Straightforward Approach Towards the C-4 functionalization of (2S)-5-oxoproline Methyl Ester

Q2 Pharmacology, Toxicology and Pharmaceutics
S. K. Panday, Munish Kumar
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引用次数: 0

Abstract

4-Substituted- 5-oxo-prolinates (pyroglutamates) are important components in various natural products, e.g. (-)-bulgecinine, (-)-anatoxin, salinosporamide, as well as ACE inhibitors. These also act as important intermediates in the synthesis of many of the bioactive molecules. Due to these reasons, the synthesis of 4-substituted-(2S)-5-oxo-prolinates has received much attention over the globe in the last three decades. However, most of the synthetic strategies available in the literature describe either the use of expensive lithium enolate-derived lowtemperature chemistry or the rigorous reaction conditions, and therefore, a simple, environmentfriendly, and cost-effective approach was truly demanding. In our ongoing research program, we required different 4-substituted pyroglutamates as intermediates, and with that very basic objective, we were looking for an alternate strategy which should be simple, requiring cheap reagents and consequently, in the process, it was thought to attempt proline catalyzed aldol/alkylation reactions on pyroglutamates, and the idea provided excellent outcome. Herein we wish to report the L-proline catalyzed asymmetric functionalization at C-4 of (2S)-5-oxoproline methyl ester, which furnished desired products at room temperature at the same time, not requiring expensive reagents and, therefore, in turn, cost-effective. This new strategy explored for synthesizing 4-substituted pyroglutamates could be useful for researchers across the globe working in the area and requiring substitution at C-4 of pyroglutamates for synthesizing bioactive molecules/natural products.
实现 (2S)-5- 氧代脯氨酸甲酯 C-4 功能化的环保型简单直接方法
4-取代-5-氧代rolinates(焦谷氨酸)是多种天然产物(如(-)-bulgecinine、(-)-anatoxin、salinosporamide以及ACE抑制剂)中的重要成分,也是合成多种生物活性分子的重要中间体。然而,文献中提供的大多数合成策略要么描述了使用昂贵的烯酸锂衍生低温化学反应,要么描述了严格的反应条件,因此真正需要的是一种简单、环境友好且具有成本效益的方法。在我们正在进行的研究项目中,我们需要不同的 4-取代焦谷氨酸盐作为中间体,基于这一基本目标,我们一直在寻找一种既简单又需要廉价试剂的替代策略,因此,在这一过程中,我们想到了尝试在焦谷氨酸盐上进行脯氨酸催化的醛醇/烷基化反应,这一想法取得了很好的结果。在此,我们希望报告 L-脯氨酸催化(2S)-5-氧代脯氨酸甲酯的 C-4 不对称官能化反应,该反应可在室温下同时得到所需的产物,不需要昂贵的试剂,因此具有成本效益。
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来源期刊
Current Bioactive Compounds
Current Bioactive Compounds Pharmacology, Toxicology and Pharmaceutics-Pharmacology, Toxicology and Pharmaceutics (all)
CiteScore
1.90
自引率
0.00%
发文量
112
期刊介绍: The journal aims to provide comprehensive review articles on new bioactive compounds with proven activities in various biological screenings and pharmacological models with a special emphasis on stereoeselective synthesis. The aim is to provide a valuable information source of bioactive compounds synthesized or isolated, which can be used for further development of pharmaceuticals by industry and academia. The journal should prove to be essential reading for pharmacologists, natural product chemists and medicinal chemists who wish to be kept informed and up-to-date with the most important developments on new bioactive compounds of natural or synthetic origin, including their stereoeselective synthesis.
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