New Picropodophyllin Analogs via Palladium-Catalyzed Allylic Alkylation− Hiyama Cross-Coupling Sequences

…, D Madec, C Kammerer, G Poli, L Girnita

Index: Vitale, Maxime; Prestat, Guillaume; Lopes, David; Madec, David; Kammerer, Claire; Poli, Giovanni; Girnita, Leonard Journal of Organic Chemistry, 2008 , vol. 73, # 15 p. 5795 - 5805

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Citation Number: 24

Abstract

Unsaturated malonyl esters underwent Pd-catalyzed intramolecular allylic alkylation to give 4-vinyl-substituted γ-lactones. In contrast to the formerly studied cyclization of malonamides, this reaction could be achieved only with a substrate incorporating a suitably positioned silicon moiety, which directs the ionization toward the desired η 3-allylpalladium complex. The resulting 4-[dimethyl-(2-thienyl) silylvinyl] lactone could be subsequently engaged ...

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