32365-96-1Relevant academic research and scientific papers
SYNTHESES WITH SULFONES XLIX: STEREO- AND ENANTIOSELECTIVE SYNTHESIS OF (S)-(-)-3,9-DIMETHYL 6-(1-METHYLETHYL) (E)-5,8-DECADIEN 1-OL ACETATE, SEXUAL PHEROMONE OF YELLOW SCALE
Alvarez, E.,Cuvigny, C.,Herve du Penhoat, C.,Julia, M.
, p. 119 - 126 (1988)
The stereo- and enantioselective synthesis of the yellow scale pheromone,(S)-(-)-3,9-dimethyl 6-(1-methylethyl) (E)-5,8-decadien 1-ol acetate, from 3-(R)-(+)-valerolactone 5 and benzene 8 is described.The key step is the in
Concise enantioselective total synthesis of neopeltolide macrolactone highlighted by ether transfer
Kartika, Rendy,Gruffi, Thomas R.,Taylor, Richard E.
supporting information; experimental part, p. 5047 - 5050 (2009/05/31)
(Chemical Equation Presented) A concise total synthesis of neopeltolide macrolactone has been accomplished in 14 steps in the longest linear sequence, 15 steps overall from commercially available materials. The present synthesis was highlighted by successful exploitation of ether transfer methodology and a radical cyclization reaction to directly establish the requisite stereochemistry of the tetrahydropyran core.
Enzymes in Organic Synthesis. 35. Stereoselective Pig Liver Esterase Catalyzed Hydrolyses of 3-Substituted Glutarate Diesters. Optimization of Enantiomeric Excess via Reaction Conditions Control
Lam, Lister K. P.,Hui, Raymond A. H. F.,Jones, J. Bryan
, p. 2047 - 2050 (2007/10/02)
Pig liver esterase catalyzed hydrolyses of C-3-substituted dimethyl glutarates are enantiotopically selective, giving acid ester products of 17-79percent ee under normal (aqueous, pH 7, 20 deg C) hydrolysis conditions.The stereoselectivity can be increased by optimizing the reaction conditions.For example, in 20percent aqueous methanol of pH 7 at -10 deg C hydrolysis of the 3-methyl diester gives the 3-methyl acid ester of 97percent ee.The hydrolysis is pro-S selective for the diesters with small C-3 substituents and reverses to pro-R preference when C-3 is large.An active site model consistent with these data is presented.
