title: Enantioselective Total Synthesis of (+)-Sieboldine A.
abstract: The first total synthesis of (+)-sieboldine A was completed starting from 5-(p-methoxybenzyloxy)pentyne in 19 steps. The enantioselective Keck allylation provided the dienyne derivative, which was exposed to the Pauson-Khand conditions to afford the bicyclo[4.3.0]nonenone derivative with high stereoselectivity with an ee value of 93%. The following Ueno-Stork reaction formed the cis-hydrindane core with a quaternary carbon center. The late-stage Schmidt glycosylation led to the formation of the N-hydroxyazacyclononane ring.
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Mohammed K
authors.initials: MK
authors.lastname: Abd El-Gaber
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Shigeo
authors.initials: S
authors.lastname: Yasuda
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Eisuke
authors.initials: E
authors.lastname: Iida
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University , Kakuma-machi, Kanazawa 920-1192, Japan.
authors.forename: Chisato
authors.identifier: 0000-0001-8621-1068
authors.initials: C
authors.lastname: Mukai