photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemicalcontrol over the radical trapping process. The phenylsulfonyl moiety, acting as a redox auxiliary group, facilitates the generation of radicals. In addition, it can eventually be removed under mild reducing conditions to reveal methyl
Stereoselective synthesis of 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane, and 5,9-dimethylheptadecane, the sex pheromones of female apple leafminer
作者:Jhillu S. Yadav、Kamakolanu Uma Gayathri、Neetipalli Thrimurtulu、Attaluri R. Prasad
DOI:10.1016/j.tet.2009.01.093
日期:2009.4
The stereoselectivesynthesis of (10R,14R)-10,14-dimethyloctadec-1-ene (1), (5R,9R)-5,9-dimethyloctadecane (2), and (5R,9R)-5,9-dimethylheptadecane (3) the sexpheromone components of female apple leafminer was accomplished by reductive elimination tosyl and isonitrile groups of dialkylated tosylmethyl isonitrile. The key steps involved were dialkylation of TosMIC with 1-iodo 2-methyl alkanes, which
to synthesize the active sex pheromone components, (S)-14-methyloctadecan-2-one ((S)-1), (S)-6-methyloctadecan-2-one ((S)-2), and their enantiomers has been developed. Key steps in the synthesis include the use of Evans’ chiral auxiliaries, Grignard cross-coupling reactions, hydroboration–oxidation, and Wacker oxidation. The synthesized sex pheromone components hold potential value for studies on communication