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通过烷氧羰基自由基环化-交叉偶联串联反应简便制备螺内酯

Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization-Cross-Coupling Cascade.

作者信息

Weires Nicholas A, Slutskyy Yuriy, Overman Larry E

机构信息

Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA, 92697-2025, USA.

Present address: Merck Research Laboratories, 2000 Galloping Hill Rd, Kenilworth, NJ, 07033, USA.

出版信息

Angew Chem Int Ed Engl. 2019 Jun 17;58(25):8561-8565. doi: 10.1002/anie.201903353. Epub 2019 May 13.

DOI:10.1002/anie.201903353
PMID:30989757
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6555670/
Abstract

An alkoxycarbonyl radical cyclization-cross-coupling cascade has been developed that allows functionalized γ-butyrolactones to be prepared in one step from simple tertiary alcohol-derived homoallylic oxalate precursors. The reaction succeeds with aryl and vinyl electrophiles and is compatible with heterocyclic fragments in both coupling partners. This chemistry allows for the rapid construction of spirolactones, which are of interest in drug discovery endeavors.

摘要

已开发出一种烷氧羰基自由基环化-交叉偶联串联反应，该反应可使官能化的γ-丁内酯从简单的叔醇衍生的高烯丙基草酸酯前体一步制备而成。该反应与芳基和乙烯基亲电试剂反应成功，并且与两个偶联伙伴中的杂环片段兼容。这种化学方法能够快速构建螺内酯，而螺内酯在药物研发中具有重要意义。

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