title: Exceedingly Concise and Elegant Synthesis of (+)-Paniculatine, (-)-Magellanine, and (+)-Magellaninone.
abstract: Starting from inexpensive (+)-pulegone as the chiral building block, a highly convergent synthesis of the unusual diquinane-based structures of (+)-paniculatine (1), (-)-magellanine (2), and (+)-magellaninone (3), has been achieved. This approach is based upon a tandem acylation-alkylation of ketoester 8 and palladium-catalyzed olefin insertion, oxidation, and hydrogenation for construction of the tetracyclic framework. This exceedingly concise strategy, requiring only 12-14 steps, is the shortest to date.
authors.affiliation: Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan R.O.C.
authors.forename: Kuo-Wei
authors.initials: KW
authors.lastname: Lin
authors.affiliation: Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan R.O.C.
authors.forename: Bakthavachalam
authors.initials: B
authors.lastname: Ananthan
authors.affiliation: Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan R.O.C.
authors.forename: Sheng-Fang
authors.initials: SF
authors.lastname: Tseng
authors.affiliation: Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan R.O.C.
authors.forename: Tu-Hsin
authors.initials: TH
authors.lastname: Yan
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000475:Alkenes; D006576:Heterocyclic Compounds, 4 or More Rings; C527464:magellaninone; C527463:paniculatine; D010165:Palladium; C471075:magellanine