STEREOSELECTIVE SYNTHESIS OF MULTIFIDENES AND RELATED STRUCTURES - CONTRIBUTION TO THE SYNTHETIC CHEMISTRY OF CIS-DISUBSTITUTED ALKEN-1-YLCYCLOPENTENES

Multifidene 8b, a major constituent of the essential oil of Cutleria multifida, was recognized as a chemical signal for gamete union. In order to test the specificity of the plant receptor system, we developed a new synthesis for structures like 8b, which combines broad variability with a high degree of stereoselectivity. Starting from a suitably functionalized derivative of dicyclopentadiene la, which allows selective transformation or introduction of side chains, a retro-dien-cleavage of the dimeric system gives easy access to homologues and structurally related compounds of the naturally occurring chemical messenger. © 1979, American Chemical Society. All rights reserved.