98524-17-5Relevant articles and documents
Regio-and enantioselective catalytic monoepoxidation of conjugated dienes: Synthesis of chiral allylic cis-epoxides
Jat, Jawahar L.,De, Saroj Ranjan,Kumar, Ganesh,Adebesin, Adeniyi Michael,Gandham, Shyam K.,Falck, John R.
supporting information, p. 1058 - 1061 (2015/03/30)
Ti(IV)-salan 4 catalyzes the diastereo-and enantioselective monoepoxidation of conjugated dienes using 30% H2O2 at rt or below even in the presence of other olefins and adjacent stereocenters. Its enantiomer, ent-4, provides access to the opposite diastereomer or enantiomer. The resultant chiral allylic epoxides, and the triols derived from them, are versatile synthetic intermediates as well as substructures present in many bioactive natural products. The epoxidation is highly specific for Z-olefins. For 1-acyl(silyl)oxypenta-2,4-dienes, epoxidation of the distal olefin is generally favored in contrast to the adjacent regioselectivity characteristic of Sharpless, peracid, and other directed epoxidations of hydroxylated dienes.
Production of hydroxy unsaturated fatty acids using crude lipoxygenase obtained from infected rice plants
Kato, Tadahiro,Watanabe, Tsutomu,Hirukawa, Toshifumi,Tomita, Norihiro,Namai, Tsuneo
, p. 1663 - 1666 (2007/10/03)
In order to explore the oxidation mode of lipoxygenase (LOX) obtained from infected rice plants, typical unsaturated fatty acids (3-8) were treated with LOX and oxygen. It was observed that ω-10 and ω-6 positions of unsaturated fatty acids were oxidized predominantly in the cases of exotic ω-6 (4 and 5) and ω-3 (7 and 8) series, respectively. In the case of endogenous fatty acids (3 and 6), oxidation at ω-6 position predominated. All the allylic alcohols obtained by reduction of the oxidation products with NaBH4 possess S-configuration.
Total enantiospecific syntheses of 13(S)-hydroxy 9Z, 11E-octadecadienoic (coriolic) acid and 13(S)-N-tosylamino analogue
Tranchepain,Le Berre,Dureault,Le Merrer,Depezay
, p. 2057 - 2065 (2007/10/02)
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