The SAMP-/RAMP -hydrazone methodology in asymmetric synthesis of 4S-ferrugineone and 4S, 5S-ferrugineol: The pheromones of palm weevils
Journal Title: Iranian Chemical Communication - Year 2014, Vol 2, Issue 2
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.The 4S, 5S-ferrugineol has been obtained with better yield (71%) and good disteromeric excess 40% de at -78 °C.
Authors and Affiliations
Dr. Hamid Saeidian, Dieter Enders, Zohreh Mirjafary
Keywords
Related Articles
- EP ID EP258467
- DOI -
- Views 112
- Downloads 0
Ag nanoparticle/melamine sulfonic acid supported on silica gel as an efficient catalytic system for synthesis of dihydropyrimidin thiones
3,4-dihydropyrimidin-2(1H)-thiones were synthesized in the presence of Ag nanoparticle/melamine sulfonic acid (MSA) supported on silica gel. The reaction was carried out at 110 oC for 20 min under solvent free conditions...
One-pot and one-step novel N-methylation of 2,6-diaminopyridine
2,6-diaminopyridine is extensively used as a pharmaceutical intermediate and a hair dye coupler as oxidation formulations. It is soluble in protic solvents. Primary and secondary amines are N-methylated by various method...
http://sci-hub.tw/10.1007/s13738-018-1312-4
Stachys is one of the largest genera in the flowering plant family. It is in the subfamily Lamioideae (Labiatae), spreading and growing in different parts of Iran. The purpose of this study was to investigate the chemica...
A cheap and an efficient electrode for electrocatalytic oxidation of methanol with nickel particles dispersed into sodium dodecyl sulfate modified carbon paste electrode
A sodium dodecyl sulfate modified carbon paste electrode (SDS/CPE) was developed in this work based on the surface modification method. The modified electrode was prepared by immersing SDS/CPE in a nickel nitrate solutio...
Tetra-N-Butyl ammonium hydroxide mediated one-pot synthesis of pyrano [2, 3-d] pyrimidinone Derivatives
Tetra-N-Butyl Ammonium Hydroxide was used as a catalyst for one-pot, three component condensation reactions consisting of aromatic aldehydes, malononitrile and barbituric acid in ethanol:water solvent system at 60oC. The...