title: Synthesis of the Core Tricyclic Ring Domain of (-)-Schulzeine B.
abstract: A formal synthesis of (-)-schulzeine B, a marine natural alkaloid possessing potent antidiabetic activity, has been achieved. A benzo[a]quinolizidin-4-one is a common skeleton of schulzeines (A-C). (-)-Schulzeine B possesses an (S)-stereogenic center at the C-3 carbon. The chiral (3S,11bS)-3-amino-9,11-dimethoxybenzo[a]quinolizidin-4-one has been prepared efficiently from (2-bromo-3,5-dihydroxyphenyl)acetonitrile in 17 steps including (i) a dehydrative intramolecular amination catalyzed by HClO4 and (ii) a proline or boric acid catalyzed transcycloamidation reaction for the construction of the δ-lactam ring.
authors.affiliation: †Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Hoshiya
authors.affiliation: †Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Kenta
authors.initials: K
authors.lastname: Noda
authors.affiliation: †Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Mihara
authors.affiliation: †Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan.|‡School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68 Koshien Kyu-bancho, Nishinomiya, 663-8179, Japan.
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Kawai
authors.affiliation: †Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Jun'ichi
authors.initials: J
authors.lastname: Uenishi
mesh_terms: D000097:Acetonitriles / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D054837:Quinolizidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C000604349:(2-bromo-3,5-dihydroxyphenyl)acetonitrile; C000604350:3-amino-9,11-dimethoxybenzo(a)quinolizidin-4-one; D000097:Acetonitriles; D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D007769:Lactams; D054837:Quinolizidines; C523671:schulzeine B