氧丙脯氨酸的实用合成

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2025-02-19 DOI:10.1021/acs.oprd.4c00521

Kelvin J. Y. Wu, Priscilla Liow, Andrew G. Myers

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引用次数: 0

摘要

提出了一种新的，更可扩展的合成抗生素候选物伊博霉素，克雷霉素和BT-33的常见氧丙脯氨酸南部片段的途径。该路线的一个关键转化是由ticl4介导的非对映选择性的烯丙基硅烷偶联加成到Evans n-丙烯酰氯唑烷酮上，然后由顺式醛醇将合成的烯醇钛加成到(R)-Garner 's醛上，这在一次操作中组装了目标分子内的所有立体中心。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Practical Synthesis of Oxepanoprolines

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Practical Synthesis of Oxepanoprolines

A new, more scalable route for the synthesis of the common oxepanoproline southern fragment of the antibiotic candidates iboxamycin, cresomycin, and BT-33 is presented. A key transformation in the route is a diastereoselective TiCl₄-mediated conjugate addition of an allylsilane to an Evans N-acryloyloxazolidinone, followed by syn-aldol addition of the resultant titanium enolate to (R)-Garner’s aldehyde, which assembles all the stereocenters within the target molecule in a single operation.

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来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

期刊介绍： The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.