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 118
- Downloads 0
Characterization of intermolecular interaction between Cl2 and HX (X=F, Cl and Br): An ab initio, DFT, NBO and AIM study
The character of the intermolecular interactions in Cl2-HX (X =F, Cl and Br) complexes has been investigated by means of the second-order Möller–Plesset perturbation theory (MP2) and the density functional theory (DFT) c...
One-pot multicomponent reaction for the synthesis of 2-amino-4-chromenes promoted by 1-methyl imidazoliumiodide [mim]Cl ionic- liquid catalyst under solvent-free conditions
simple, clean, and environmentally benign three-component process for the synthesis of 2-amino-4Hchromenes using [mim]Cl, as an efficient catalyst under solvent-free conditions are described. A wide range of aromatic ald...
Synthesis of some network polymers with siloxane units as a drug delivery system
New biodegradable network polymers containing siloxane-linked polymeric prodrugs of 5-ammino-2-hydroxybenzoic acid (5-ASA) in the main chain were prepared by ter polymerization of methacrylic acid (MA), 2-hydroxyethylmet...
Surfactant-assisted synthesis of Barium hexaferrite nanoparticles by hydrothermal method
In the present work, the synthesis of Barium hexaferrite (BaFe12O19) nanoparticles in the presence of a large excess amount of OH− anions by the hydrothermal method in the presence and absence of surfactants such as Sodi...
Fe3O4@SiO2-SO3H as a recyclable heterogeneous nanomagnetic catalyst for the one-pot synthesis of substituted quinolines via Friedländer heteroannulation under solvent-free conditions
An efficient method has been developed for the Friedländer synthesis of substituted quinolines through a condensation reaction of 2-aminoaryl ketones with α-methylene ketones in the presence of a catalytic amount of nano...