title: Asymmetric synthesis of the tricyclic core of Calyciphylline A-type alkaloids via intramolecular [3 + 2] cycloaddition.
abstract: Asymmetric synthesis of the [5-6-7] tricyclic system common to the Calyciphylline A-type alkaloids is reported, featuring Overman rearrangement, Heck cyclization, intramolecular [3 + 2] cycloaddition, diastereoselective hydrogenation, and Claisen rearrangement as strategic events. The approach is capable of installing the crucial carbonyl functionality as well as multiple stereogenic centers within a congested polycyclic ring skeleton.
authors: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University , Shenzhen 518055, China.
authors: Lu
authors: L
authors: Wang
authors: Chen
authors: C
authors: Xu
authors: Li
authors: L
authors: Chen
authors: Xiaojiang
authors: X
authors: Hao
authors: David Zhigang
authors: DZ
authors: Wang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D061565:Cycloaddition Reaction; D006865:Hydrogenation; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D031995:Saxifragaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011083:Polycyclic Compounds; C479143:calyciphylline A