| Abstract
| - The synthesis of a spiro[4.4]nonane skeleton by the palladium-catalyzed domino cyclization of a linear7-methylene-2,10-undecadienyl acetate is described. The π-allylpalladium intermediate underwentintramolecular alkene insertion with high intraannular diastereoselectivity, followed by intramolecularHeck-type cyclization, leading to a spiro[4.4]nonane system. Oxidation of the allylic ether moiety andtransformation of the vinyl group to an exo-methylene unit provided 3, which is the known syntheticintermediate of dimethyl gloiosiphone A (2).
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