title: Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (-)-Calycanthine.
abstract: Facile, straightforward, and asymmetric total syntheses of (+)-chimonanthine (1), (+)-folicanthine (2), and (-)-calycanthine (3) were accomplished in four to five steps from commercially available tryptamine. The synthesis features copper-mediated asymmetric cyclodimerization of chiral tryptamine derivative, which established a new entry into constructing the sterically hindered vicinal quaternary stereogenic carbon centers of dimeric hexahydropyrroloindole alkaloids in one procedure. An unprecedented base-induced isomerization from the chimonanthine skeleton to the calycanthine skeleton was observed and facilitated the synthesis of (-)-calycanthine (3).
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University , Kunming 650091, China.|State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.|University of Chinese Academy of Sciences , Beijing 100049, China.
authors.forename: Ming
authors.initials: M
authors.lastname: Ding
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.|University of Chinese Academy of Sciences , Beijing 100049, China.
authors.forename: Kangjiang
authors.initials: K
authors.lastname: Liang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.
authors.forename: Rui
authors.initials: R
authors.lastname: Pan
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University , Kunming 650091, China.
authors.forename: Hongbin
authors.initials: H
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University , Kunming 650091, China.|State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.
authors.forename: Chengfeng
authors.initials: C
authors.lastname: Xia
mesh_terms: D002384:Catalysis; D026121:Indole Alkaloids / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D007211:Indoles; D009287:Naphthyridines; D011758:Pyrroles; C521485:folicanthine; C521484:chimonanthine; C070236:calycanthine