Carbonyl Activation in Electrophilic Polyene Cyclizations: A Toolbox for the Design of Isoprenoid Libraries

Alberto Minassi, Federica Pollastro, Giuseppina Chianese, Diego Caprioglio, Orazio Taglialatela-Scafati, Giovanni Appendino

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

An approach to biogenetically overlooked areas of the isoprenoid chemical space is presented. This strategy is based on the generation of a cationic center in functionalized polyolefins by Lewis acid activation of a carbonyl group, rather than by electrophilic attack at a double bond. Starting from the monocyclic humulane trienone zerumbone, polycyclic sesquiterpenoid skeletons which are either not reported as natural products or biogenetically enigmatic in terms of the isoprenoid rule, were obtained by modulating the Lewis acid catalyst. In the course of these studies, the surprising formation of a strained E-cyclooctene motif was observed in a cyclization reaction.

Lingua originaleInglese
pagine (da-a)7935-7938
Numero di pagine4
RivistaAngewandte Chemie - International Edition
Volume56
Numero di pubblicazione27
DOI
Stato di pubblicazionePubblicato - 26 giu 2017

Fingerprint

Entra nei temi di ricerca di 'Carbonyl Activation in Electrophilic Polyene Cyclizations: A Toolbox for the Design of Isoprenoid Libraries'. Insieme formano una fingerprint unica.

Cita questo