Total synthesis of (+)-manzamine A.
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.
Toma
Tatsuya
T
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kita
Yoichi
Y
Fukuyama
Tohru
T
D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D013237:Stereoisomerism
D002227:Carbazoles; C078290:manzamine A