Dedicated to Barbara, Kurt, and Konrad Krieger

Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry

Abstract

Benzilic acid rearrangement of i-steroid ketones and their subsequent opening gives access to 5(6→7)abeo-steroids. The functional group tolerance is demonstrated by several examples, including substrates with additional olefinic groups. The method opens a potential route to the synthesis of complex natural products such as solanioic acid from abundant steroid starting materials like ergosterol.

Benzilic acid rearrangement of i-steroid ketones and their subsequent opening gives access to 5(6→7)abeo-steroids. The functional group tolerance is demonstrated by several examples, including substrates with additional olefinic groups. The method opens a potential route to the synthesis of complex natural products such as solanioic acid from abundant steroid starting materials like ergosterol.

中文翻译：

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通过i-类固醇的苯甲酸重排获得5（6→7）阿拉伯-类固醇

致力于Barbara，Kurt和Konrad Krieger

作为Bürgenstock专栏2017年有机化学中的未来之星的一部分发布

抽象的

的二苯乙醇酸重排我-steroid酮和它们随后的开口可以访问5（6→7）的abeo- -steroids。几个实例证明了官能团的耐受性，包括具有附加烯基的底物。该方法为从丰富的甾体原料如麦角固醇合成复杂的天然产物（如茄酸）开辟了一条可能的途径。

的二苯乙醇酸重排我-steroid酮和它们随后的开口可以访问5（6→7）的abeo- -steroids。几个实例证明了官能团的耐受性，包括具有附加烯基的底物。该方法为从丰富的甾体原料如麦角固醇合成复杂的天然产物（如茄酸）开辟了一条可能的途径。