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.
Photoinduced Decarbonylative Rearrangement of Bicyclo[2.2.2]octenones: Synthesis of the Marasmane Skeleton. -The fused-5,6,3-tricyclic ring structure of the marasmane sesquiterpenoid skeleton is formed via a photo-induced decarbonylative 1,3-migration reaction of bicyclo[2.2.2]octenone derivatives such as (I), (III), and (V). -(WANG, C.-C.; KU, Y.-C.; CHUANG*, G. J.; J. Org. Chem. 80 (2015) 21, 10979-10991, http://dx.doi.org/10.1021/acs.joc.5b02140 ; Dep. Chem., Chung-Yuan Christian Univ., Chung-Li, Taiwan; Eng.) -M. Paetzel 11-035
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