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The SAMP-/RAMP -hydrazone methodology in asymmetric synthesis of 4S-ferrugineone and 4S, 5S-ferrugineol: The pheromones of palm weevils | ||
Iranian chemical communication | ||
مقاله 6، دوره 2، Issue 2, pp. 82-163, Serial No. 3، تیر 2014، صفحه 137-146 اصل مقاله (624.78 K) | ||
نوع مقاله: Original Research Article | ||
نویسندگان | ||
Hamid Saeidian* 1؛ Dieter Enders2؛ Zohreh Mirjafary3 | ||
1Department of Science, Payame Noor University (PNU), PO Box: 19395-4697, Tehran, Iran | ||
2Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany | ||
3Department of Chemistry, Science and Research Branch Islamic Azad University, Tehran, Iran | ||
چکیده | ||
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.The 4S, 5S-ferrugineol has been obtained with better yield (71%) and good disteromeric excess 40% de at -78 °C. | ||
کلیدواژهها | ||
Pheromone؛ 4S-ferrugineone؛ 4S؛ 5S-ferrugineol؛ SAMP/RAMP hydrazone | ||
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