title: Total synthesis of (-)-haouamine B pentaacetate and structural revision of haouamine B.
abstract: The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused β-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the β-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubía.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Momoi
authors.forename: Kei-ichiro
authors.initials: K
authors.lastname: Okuyama
authors.forename: Hiroki
authors.initials: H
authors.lastname: Toya
authors.forename: Kenji
authors.initials: K
authors.lastname: Sugimoto
authors.forename: Kentaro
authors.initials: K
authors.lastname: Okano
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Tokuyama
mesh_terms: D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D000097566:Cyclophanes
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; C474768:haouamine B; D000097566:Cyclophanes
keywords: alkaloids; aromatic substitution; cross-coupling; cyclization; total synthesis