Photoinduced Decarbonylative Rearrangement of Bicyclo[2.2.2]Octenones: Synthesis of the Marasmane Skeleton

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• 作者：Chun-Chieh Wang ; Yi-Chen Ku ; Gary Jing Chuang
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：80
• 期：21
• 页码：10979-10991
• 全文大小：618K
• ISSN：1520-6904

文摘

The marasmane sesquiterpenoid structure can be found in the skeleton of a variety of natural products bearing interesting bioactivity. The unique fused-5,6,3-tricyclic ring structure, in which the rings are cis-fused and the five- and three-membered rings are mutually trans, provides a synthetic challenge for organic chemists. In this work, we took advantage of the photoinduced decarbonylative rearrangement of bicyclo[2.2.2]octenone to develop a new methodology for construction of the highly functionalized fused-5,6,3-tricyclic ring structure in a concise reaction sequence.