title: Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)-Haplophytine by Direct Coupling and Late-Stage Oxidative Rearrangement.
abstract: A bioinspired convergent total synthesis of (+)-haplophytine, a dimeric indole alkaloid with diazabicyclo[3.3.1]nonane and hexacyclic aspidosperma segments, is described. This synthesis involves the direct coupling of the two segments in a AgNTf2-mediated Friedel-Crafts reaction and construction of the diazabicyclo[3.3.1]nonane skeleton through late-stage chemoselective aerobic oxidation of the 1,2-diaminoethene moiety and a sequential semipinacol-type rearrangement.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba 6-3, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Satoh
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba 6-3, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
authors.forename: Ken-Ichi
authors.initials: KI
authors.lastname: Ojima
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba 6-3, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Ueda
authors.affiliation: Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba 6-3, Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Tokuyama
keywords: Friedel-Crafts reaction; alkaloids; oxidation; rearrangement; total synthesis