title: Redox divergent synthesis of fawcettimine-type Lycopodium alkaloids.
abstract: A new approach for synthesis of fawcettimine-type Lycopodium alkaloids is described. A divergent strategy was achieved by applying stereoselective Diels-Alder reaction followed by redox-controlled elaboration. Eventually, (-)-8-deoxyserratinine, (+)-fawcettimine, (-)-lycopoclavamine-A, (-)-serratine, (-)-lycopoclavamine-B and (-)-serratanidine were successfully accessed.
authors.affiliation: School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192 (Japan).
authors.forename: Hisaaki
authors.initials: H
authors.lastname: Zaimoku
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Taniguchi
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D061565:Cycloaddition Reaction; D032502:Lycopodium / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C524731:fawcettimine
keywords: asymmetric synthesis; cycloaddition; divergent synthesis; natural products; total synthesis