Abstract
The coupling of 2-(tributylstannyl)cyclopent-2-enone with several (π-allyl)palladium complexes derived from allylic electrophiles was investigated as the key step in the synthesis of jasmonoids. These compounds have an important role in plant development, triggering direct and indirect responses when harmed to induce pest resistance. Palladium-catalyzed coupling conditions to obtain a jasmonoid library are described. The retention of geometry of the olefin in the allyl group is not always observed due to syn-anti isomerization of the (π-allyl)palladium complex. The methodology was employed for the synthesis of a simplified jasmonic acid analog.
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