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Carbonyl Activation in Electrophilic Polyene Cyclizations: A Toolbox for the Design of Isoprenoid Libraries. 2017
Alberto Minassi, and
Federica Pollastro, and
Giuseppina Chianese, and
Diego Caprioglio, and
Orazio Taglialatela-Scafati, and
Giovanni Appendino
Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, L.go Donegani 2, 28100, Novara, Italy.
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.
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