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Stereoselective synthesis of multifidenes and related structures synthetic chemistry of cis di substituted alken 1 yl cyclo pentenes


, : Stereoselective synthesis of multifidenes and related structures synthetic chemistry of cis di substituted alken 1 yl cyclo pentenes. Journal of Organic Chemistry 44(26): 4819-4824

Multifidene 8b, a major constituent of the essential oil of the seaweed, Cutleria multifida, was recognized as a chemical signal for gamete union. To test the specificity of the plant receptor system, a new synthesis for structures like 8b was developed, which combines broad variability with a high degree of stereoselectivity. Starting from a suitably functionalized derivative of dicyclopentadiene, which allows selective transformation or introduction of side chains, a retro-dien-cleavage of the dimeric system gives easy access to homologes and structurally related compounds of the naturally occurring chemical messenger [released by unfertilized mature females].

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