95340-95-7Relevant academic research and scientific papers
Enzymes in Organic Synthesis. 34. Preparations of Enantiomerically Pure Exo-and Endo-Bridged Bicyclic and Chiral Lactones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Meso Diols
Lok, Kar P.,Jakovac, Ignac J.,Jones, J.Bryan
, p. 2521 - 2526 (1985)
Preparative-scale horse liver alcohol dehydrogenase catalyzed oxidations of saturated and unsaturated exo- and endo-bridged bicyclic and meso diols proceed with complete enantiotopic specificity to give high (64-87percent) yields of the corresponding chiral lactones of >=97percent ee.As for previous meso diol oxidations, the stereochemical course of each oxidation (S-center CH2OH oxidation in all cases) is as predicted by the cubic-space model of the active site.An illustration of the asymmetric synthetic value of these chiral lactones is provided by the conversion of one of them into a prostaglandin precursor.
Synthesis and insecticidal activity of lactones derived from furan-2(5H)-one
Teixeira, Milena G.,Alvarenga, Elson S.,Pimentel, Mirian F.,Pican?o, Marcelo C.
, p. 2279 - 2289 (2015/11/10)
Ten 4,7-methanoisobenzofuran-1(3H)-ones were synthesized and their insecticidal activities against the insect pest Diaphania hyalinata were evaluated. The most active substances have been selected from the initial screening to find the dose to kill 50 (LD50) and 90percent (LD90) of the melonworm. Time-mortality curves of the three selected formulations at the LD90 concentration have been made against D. hyalinata. From the time-mortality curves we found that the formulation (3aR,4R,5S,6S,7S,7aS)- and (3aS,4S,5R,6R,7R,7aR)-5,6-dichlorohexahydro-4,7-methanoisobenzofuran-1(3H)-one + (3aR,4R,5R,6R,7S,7aS)- and (3aS,4S,5S,6S,7R,7aR)-5,6-dichlorohexahydro-4,7-methanoisobenzofuran-1(3H)-one has killed 50percent of the melonworm after 2 h, presenting the best knockdown effect. Bioassays against Solenopsis saevissima and Tetragonisca angustula were carried out for the lactones selected in the initial screening against D. hyalinata. The formulation (3aS,4R,5S,6S,7S,7aR)- and (3aR,4S,5R,6R,7R,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one + (3aS,4R,5R,6R,7S,7aR)- and (3aR,4S,5S,6S,7R,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one has killed 31.25 and 68.30percent of the pest natural enemy and the pollinator bee, respectively. At the same concentration this formulation killed 90percent of D. hyalinata. The selectivity in favor of the non-target organisms has rendered this formulation a position as a promising agrochemical.
