螺环氧环己二烯酮的环加成、激发态下的自由基环化和 1,3-酰基迁移：芳烃到甾醇-4-酮。
Cycloaddition of Spiroepoxycyclohexa-2,4-dienones, Radical Cyclization and 1,3-Acyl Shift in Excited State: Aromatics to Sterpuren-4-one.
机构信息
Department of Chemistry, Indian Institute of Technology Bombay , Mumbai 400076, India.
出版信息
J Org Chem. 2017 Jun 16;82(12):6268-6278. doi: 10.1021/acs.joc.7b00867. Epub 2017 Jun 7.
PMID:28552002
Abstract
A stereoselective route to sterpuren-4-one from a simple aromatic precursor is presented. Oxidative dearomatization, πs + πs cycloaddition of 6,6-spiroepoxycyclohexa-2,4-dienones with ethyl acrylate, radical cyclization and 1,3-acyl shift in excited state are the important aspects of our approach. An interesting effect of a remote substituent on radical cyclization has also been presented.
摘要
本文提出了一种从简单芳香前体立体选择性合成甾醇酮-4-酮的方法。氧化去芳构化、6,6-螺环氧环己-2,4-二烯酮与丙烯酸乙酯的πs+πs 环加成、激发态下的自由基环化和 1,3-酰基迁移是我们方法的重要方面。还提出了远程取代基对自由基环化的有趣影响。
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