title: Asymmetric total synthesis of caribenol A via an intramolecular Diels-Alder reaction.
abstract: A total synthesis of the caribenol A (1), a novel natural product with an intriguing tetracyclic framework, has been achieved. The synthesis features an intramolecular Diels-Alder (IMDA) reaction for the facile construction of the tricyclic [5-7-6] skeleton of caribenol A (1) and a biomimetic oxidation reaction for the formation of the 2-hydroxyfuran-2(5H)-one motif of caribenol A (1) as key steps. This synthetic approach also reveals that the sp(2) carbon at C(2) in substrate 8 is a critical factor for the formation of the tricyclic [5-7-6] skeleton in 7.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, China 518055.
authors.forename: Jing-Chun
authors.initials: JC
authors.lastname: Han
authors.forename: Lian-Zhu
authors.initials: LZ
authors.lastname: Liu
authors.forename: Yuan-Yuan
authors.initials: YY
authors.lastname: Chang
authors.forename: Guo-Zong
authors.initials: GZ
authors.lastname: Yue
authors.forename: Jie
authors.initials: J
authors.lastname: Guo
authors.forename: Li-Yan
authors.initials: LY
authors.lastname: Zhou
authors.forename: Chuang-Chuang
authors.initials: CC
authors.lastname: Li
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D004224:Diterpenes; C555112:caribenol A