title: Photoinduced Decarbonylative Rearrangement of Bicyclo[2.2.2]Octenones: Synthesis of the Marasmane Skeleton.
abstract: 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.
authors.affiliation: Department of Chemistry, Chung Yuan Christian University , Chung-Li, Taiwan.
authors.forename: Chun-Chieh
authors.initials: CC
authors.lastname: Wang
authors.affiliation: Department of Chemistry, Chung Yuan Christian University , Chung-Li, Taiwan.
authors.forename: Yi-Chen
authors.initials: YC
authors.lastname: Ku
authors.affiliation: Department of Chemistry, Chung Yuan Christian University , Chung-Li, Taiwan.
authors.forename: Gary Jing
authors.initials: GJ
authors.lastname: Chuang
mesh_terms: D001669:Biochemical Phenomena; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; D034242:Cyclooctanes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C000606349:marasmane