Author/Authors :
سعيديان، حميد نويسنده Department of Chemistry, Payame Noor University, P.O. BOX 19395-4697, Tehran, Iran Saeidian, Hamid , اندرس، ديتر نويسنده bInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany Enders , Dieter , ميرجعفري، زهره نويسنده Department of Chemistry, Science and Research Branch Islamic Azad University, Tehran, Iran Mirjafary, Zohreh
Abstract :
4S-ferrugineone and 4S,5S-ferrugineol as pheromones of palm weevils were synthesized in 3 and 4 steps, respectively, starting from nonane-5-one employing SAMP-/RAMP -hydrazone methodology. 5-Nonanone is transformed to its corresponding RAMP hydrazone by reaction with the enantiomerically pure hydrazine RAMP. Metalation with lithium diisopropylamide (LDA) in ether to form azaenolate, followed by methylation with methyl iodide, furnishes the product hydrazone. Finally, cleavage of the hydrazone moiety to regenerate the carbonyl functionality is possible by ozonolysis, leads to the 4S-ferrugineone. The crucial step would be the final diastereoselective reduction to the 4S, 5S-ferrugineol.
