title: Collective total synthesis of tetracyclic diquinane Lycopodium alkaloids (+)-paniculatine, (-)-magellanine, (+)-magellaninone and analogues thereof.
abstract: The collective total synthesis of tetracyclic diquinane Lycopodium alkaloids, (+)-paniculatine, (-)-magellanine, (+)-magellaninone, and two analogues (-)-13-epi-paniculatine and (+)-3-hydroxyl-13-dehydro-paniculatine, has been accomplished. By logic-guided addition of a strategically useful hydroxyl group at C-3 of paniculatine, the formidable tetracyclic core was rapidly synthesized utilizing a site-specific and stereoselective aldol cyclization, thus making the ABD → ABCD tetracyclic approach to diquinane Lycopodium alkaloids attainable for the first time.
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: Shi-Zhi
authors.initials: SZ
authors.lastname: Jiang
authors.forename: Ting
authors.initials: T
authors.lastname: Lei
authors.forename: Kun
authors.initials: K
authors.lastname: Wei
authors.forename: Yu-Rong
authors.initials: YR
authors.lastname: Yang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: C000594805:3-hydroxyl-13-dehydro-paniculatine; D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C527464:magellaninone; C527463:paniculatine; C471075:magellanine