title: Total synthesis of (+)-manzamine A.
abstract: A novel synthetic route to (+)-manzamine A was developed. It highlights an amazingly efficient construction of a highly strained 15-membered ring across a cyclohexenone ring with the aim of installing the requisite functionalities in a completely stereocontrolled manner. Other key features include a stereoselective Diels-Alder reaction of an optically active butenolide, construction of the 15-membered ring by intramolecular Mitsunobu reaction of a nosyl amide, [3,3]-sigmatropic rearrangement of allyl cyanate for stereoselective introduction of nitrogen functionality at a sterically congested position, and a ring-closing metathesis in the presence of labile functional groups.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Toma
authors.forename: Yoichi
authors.initials: Y
authors.lastname: Kita
authors.forename: Tohru
authors.initials: T
authors.lastname: Fukuyama
mesh_terms: D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D013237:Stereoisomerism
chemical_list: D002227:Carbazoles; C078290:manzamine A