title: Total syntheses of leuconoxine, leuconodine B, and melodinine E by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis.
abstract: Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University , Aoba 6-3, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Umehara
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Ueda
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Tokuyama
mesh_terms: D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D046948:Secologanin Tryptamine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D046948:Secologanin Tryptamine Alkaloids; C000591793:leuconodine B; C000590191:leuconoxine; C000591794:melodinine E