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Synlett 1991; 1991(1): 53-56
DOI: 10.1055/s-1991-20627
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Model Studies of Palladium-Catalysed Coupling Reactions for the "South-North" Attachment of Avermectins

Jean Pierre Férézou* , Marc Julia, Yun Li, Lu Wei Liu, Ange Pancrazi
  • *Laboratoire de Chimie, École Normale Supérieure, 24 rue Lhomond, F-75231 Paris Cedex 05, France
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07. März 2002 (online)

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Model palladium-catalysed vinyl-vinyl coupling reactions have been tested for the construction of the 8E,10E-diene system of avermectins. Cross coupling of the southern bicylic vinyl iodide ethyl 3-iodomethylene-3a-(trimethylsiloxy)octahydrobenzo-furan-4-carboxylate, prepared from ethyl 2-oxocyclohexanecarboxylate, with northern 1-alkenylstannanes or the one-carbon-homologation reagent tributyl(4-methoxybenzyloxymethyl)-stannane has been shown to occur with acceptable yields.