title: Asymmetric, protecting-group-free total synthesis of (+)-caribenol A.
abstract: Caribenol Queen: A new asymmetric, protecting-group-free synthesis of the marine tetracyclic diterpenoid (+)-caribenol A (1) has been achieved. The enantioselective synthesis employed (S)-methyl 1-methyl-2-oxocyclopent-3-enecarboxylate as a chiral scaffold, and an intramolecular Diels-Alder (IMDA) reaction of substrate 3 afforded the [5.7.6] tricyclic core in compound 2.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen 518055, China.
authors.forename: Jing-Chun
authors.initials: JC
authors.lastname: Han
authors.forename: Lian-Zhu
authors.initials: LZ
authors.lastname: Liu
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; D061565:Cycloaddition Reaction; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C555112:caribenol A
keywords: Diels-Alder reaction; asymmetric synthesis; intramolecular; synthetic methods; total synthesis