Total Synthesis and Structural Revision of the Piperarborenines via Sequential Cyclobutane C鈥揌 Arylation

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• 作者：Will R. Gutekunst ; Phil S. Baran
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：November 30, 2011
• 年：2011
• 卷：133
• 期：47
• 页码：19076-19079
• 全文大小：811K
• 年卷期：v.133,no.47(November 30, 2011)
• ISSN：1520-5126

文摘

A strategy for the construction of unsymmetrical cyclobutanes using C鈥揌 functionalization logic is demonstrated in the total synthesis of piperarborenine B and piperarborenine D (reported structure). These syntheses feature a new preparation of cis-cyclobutane dicarboxylates from commercially available coumalate starting materials and a divergent approach to the controlled cis or trans installation of the two distinct aryl rings found in the natural products using the first example of cyclobutane C鈥揌 arylation. The structure of piperarborenine D is reassigned to a head-to-head dimer, which was synthesized using an intramolecular [2+2] photocycloaddition strategy.