title: Total Synthesis of (±)-Kuwanol E.
abstract: The total synthesis of the Diels-Alder-type adducts (±)-kuwanol E and the heptamethyl ether derivative of (±)-kuwanon Y has been accomplished via a convergent strategy involving 2'-hydroxychalcone 6 or 9 and dehydroprenylstilbene 7, in nine steps. The synthesis features, as a key step, a Lewis acid-mediated biomimetic intermolecular Diels-Alder [4+2] cycloaddition for the construction of the cyclohexene skeleton with three stereogenic centers. Notably, the endo/exo diastereoselectivity of the reaction proved to be temperature-controlled.
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma , p.le Aldo Moro 5, 00185 Roma, Italy.|Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia , Viale Regina Elena 291, 00161 Roma, Italy.
authors.forename: Valentina
authors.initials: V
authors.lastname: Iovine
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma , p.le Aldo Moro 5, 00185 Roma, Italy.
authors.forename: Irene
authors.initials: I
authors.lastname: Benni
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma , p.le Aldo Moro 5, 00185 Roma, Italy.
authors.forename: Rocchina
authors.initials: R
authors.lastname: Sabia
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma , p.le Aldo Moro 5, 00185 Roma, Italy.
authors.forename: Ilaria
authors.initials: I
authors.lastname: D'Acquarica
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma , p.le Aldo Moro 5, 00185 Roma, Italy.
authors.forename: Giancarlo
authors.initials: G
authors.lastname: Fabrizi
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma , p.le Aldo Moro 5, 00185 Roma, Italy.|Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia , Viale Regina Elena 291, 00161 Roma, Italy.
authors.forename: Bruno
authors.initials: B
authors.lastname: Botta
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma , p.le Aldo Moro 5, 00185 Roma, Italy.|Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia , Viale Regina Elena 291, 00161 Roma, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Calcaterra
mesh_terms: D047188:Chalcones; D053138:Cyclohexenes; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D047188:Chalcones; D053138:Cyclohexenes; D005419:Flavonoids; C000620403:kuwanol E; C052568:cyclohexene; C013031:2'-hydroxychalcone