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.
Total Synthesis of (±)-Kuwanol E / Iovine, Valentina; Benni, Irene; Sabia, Rocchina; D'Acquarica, Ilaria; Fabrizi, Giancarlo; Botta, Bruno; Calcaterra, Andrea. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 1520-6025. - ELETTRONICO. - 10:79(2016), pp. 2495-2503. [10.1021/acs.jnatprod.6b00350]
Total Synthesis of (±)-Kuwanol E
IOVINE, VALENTINAPrimo
;BENNI, IRENESecondo
;SABIA, ROCCHINA;D'ACQUARICA, Ilaria
;FABRIZI, Giancarlo;BOTTA, Bruno
Penultimo
;CALCATERRA, ANDREAUltimo
2016
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
