Over the years secondary metabolites have been considered as lead molecules both in their natural form and as templates for medicinal chemistry. Some secondary metabolites such as polyphenols and flavan-3-ols exert beneficial effects after a modification by the microbiota. Synthetic precursors of some of these modified compounds, in turn, carried a γ-alkylidenebutenolide moiety which characterizes a large class of bioactive natural products endowed with a wide range of biological activities. For these reasons stereoselective preparation of γ-alkylidenebutenolide continues to be an important issue for organic chemists. Our objective is to synthetize the novel compound (Z)-5-(3′,4′-bis(benzyloxy)benzylidene)furan-2(5H)-one in a stereocontrolled-one-pot reaction. The product was obtained in good yield. Furthermore, the theoretical investigation of the transition states suggests a new procedure to achieve Z-isomer of β-unsubstituted γ-alkylidenebutenolide
(Z)-5-(3′,4′-Bis(benzyloxy)benzylidene)furan-2(5H)-one / A. Artasensi, G. Baron, G. Vistoli, G. Aldini, L. Fumagalli. - In: MOLBANK. - ISSN 1422-8599. - 2021:1(2021 Feb 28), pp. M1193.1-M1193.8.
FUMAGALLI, LAURA (Corresponding)
|Parole Chiave:||γ-alkylidenebutenolide; secondary metabolite; polyphenols; β-unsubstituted γ-alkylidenebutenolide|
|Settore Scientifico Disciplinare:||Settore CHIM/08 - Chimica Farmaceutica|
|Data di pubblicazione:||28-feb-2021|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.3390/M1193|
|Appare nelle tipologie:||01 - Articolo su periodico|