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گواهی نمایه سازی مقاله The SAMP-/RAMP-hydrazone methodology in asymmetric synthesis of 4S-ferrugineone and 4S,5S-ferrugineol: The pheromones of palm weevils

عنوان مقاله: The SAMP-/RAMP-hydrazone methodology in asymmetric synthesis of 4S-ferrugineone and 4S,5S-ferrugineol: The pheromones of palm weevils
شناسه (COI) مقاله: JR_ICC-2-2_006
منتشر شده در فصلنامه ارتباطات شیمی ایران در سال ۱۳۹۳
مشخصات نویسندگان مقاله:

Hamid Saeidian - Department of Science, Payame Noor University, P.O. Box 19395-4697, Tehran, Iran
Dieter Enders - Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany
Zohreh Mirjafary - Department of Chemistry, Science and Research Branch Islamic Azad University, Tehran, Iran

خلاصه مقاله:
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.

کلمات کلیدی:
Pheromone, 4S-ferrugineone, 4S,5S-ferrugineol, SAMP , RAMP hydrazone

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