title: Biomimetic total synthesis of (+)-chabranol.
abstract: A concise, biomimetic total synthesis of the unprecedented terpenoid skeleton (+)-chabraol has been accomplished via 6 steps from the chiral epoxide 7, involving an intramolecular Prins double cyclization to yield the bicyclo[2.2.1] core of the natural product as the key step. The absolute configuration of natural chabranol was also designated through the first asymmetric total synthesis.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Xiaolei
authors.initials: X
authors.lastname: Wang
authors.forename: Jie
authors.initials: J
authors.lastname: Zheng
authors.forename: Qiang
authors.initials: Q
authors.lastname: Chen
authors.forename: Huaiji
authors.initials: H
authors.lastname: Zheng
authors.forename: Yongping
authors.initials: Y
authors.lastname: He
authors.forename: Juan
authors.initials: J
authors.lastname: Yang
authors.forename: Xuegong
authors.initials: X
authors.lastname: She
mesh_terms: D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013729:Terpenes; C545600:chabranol