韦利他汀支持研究：芳基铅（IV）偶联反应的扩展与局限
Welwistatin support studies: expansion and limitation of aryllead(IV) coupling reactions.
作者信息
Xia Jibo, Brown Lauren E, Konopelski Joseph P
机构信息
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
出版信息
J Org Chem. 2007 Aug 31;72(18):6885-90. doi: 10.1021/jo071156l. Epub 2007 Aug 9.
Abstract
Recent support studies on the total synthesis of the welwistatin system are described. The target step involves lead-mediated arylation of sterically demanding aryl groups and carbon acid coupling partners in order to establish the highly congested tetracyclic core structure. Type 7 beta-ketoesters and beta-ketonitriles were successfully arylated with a variety of ortho- and meta-substituted aryllead compounds generated by a halogen-boron-lead exchange sequence. The enolates of compounds 15, 19, and 25, each bearing all-carbon quaternary centers adjacent to the arylation site, failed to couple.
摘要
本文描述了近期关于威氏他汀系统全合成的支持性研究。目标步骤涉及在空间位阻较大的芳基和碳酸耦合伙伴之间进行铅介导的芳基化反应，以构建高度拥挤的四环核心结构。通过卤素-硼-铅交换序列生成的各种邻位和间位取代的芳基铅化合物成功地与7型β-酮酯和β-酮腈发生了芳基化反应。化合物15、19和25的烯醇盐，每个在芳基化位点附近都带有全碳季碳中心，未能发生偶联反应。
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