ENZYMATIC DESYMMETRIZATION OF MESO-2,6-DIMETHYL-1,7-HEPTANEDIOL - ENANTIOSELECTIVE FORMAL SYNTHESIS OF THE VITAMIN-E SIDE-CHAIN AND THE INSECT PHEROMONE TRIBOLURE

Authors
CHENEVERT R DESJARDINS M
Citation
R. Chenevert et M. Desjardins, ENZYMATIC DESYMMETRIZATION OF MESO-2,6-DIMETHYL-1,7-HEPTANEDIOL - ENANTIOSELECTIVE FORMAL SYNTHESIS OF THE VITAMIN-E SIDE-CHAIN AND THE INSECT PHEROMONE TRIBOLURE, Journal of organic chemistry, 61(4), 1996, pp. 1219-1222
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
4
Year of publication
1996
Pages
1219 - 1222
Database
ISI
SICI code
0022-3263(1996)61:4<1219:EDOM-E>2.0.ZU;2-N
Abstract
The chiral syn-1,5-dimethylalkyl subunit is found in many natural prod ucts with significant biological activities. Enzymatic esterification of meso-2,6-dimethyl-1,7-heptanediol with isopropenyl acetate in the p resence of Pseudomonas cepacia lipase in organic medium provided the c hiral nonracemic monoester in high enantiomeric excess (ee = 95%). Thi s chiral building block was used in the formal syntheses of vitamin E side chain and the insect pheromone tribolure.