Enzymatic desymmetrization of meso-2,6-dimethyl-1,7-heptanediol. Enantioselective formal synthesis of the vitamin E side chain and the insect pheromone tribolure

被引：28

作者：

Chenevert, R

Desjardins, M

机构：

[1] Département de Chimie, Fac. des Sci. et de Genie, Université Laval, Québec

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 04期

关键词：

D O I：

10.1021/jo9516650

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral syn-1,5-dimethylalkyl subunit is found in many natural products with significant biological activities. Enzymatic esterification of meso-2,6-dimethyl-1,7-heptanediol with isopropenyl acetate in the presence of Pseudomonas cepacia lipase in organic medium provided the chiral nonracemic monoester in high enantiomeric excess (ee = 95%). This chiral building block was used in the formal syntheses of vitamin E side chain and the insect pheromone tribolure.

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页码：1219 / 1222

页数：4

相关论文

共 45 条

[1] IDENTIFICATION OF MALE-SPECIFIC VOLATILES FROM NEARCTIC AND NEOTROPICAL STINK BUGS (HETEROPTERA, PENTATOMIDAE) [J].

ALDRICH, JR ;

OLIVER, JE ;

LUSBY, WR ;

KOCHANSKY, JP ;

BORGES, M .

JOURNAL OF CHEMICAL ECOLOGY, 1994, 20 (05) :1103-1111

[2] 1,5-ACYCLIC STEREOSELECTION - THE STEREOCONTROLLED SYNTHESIS OF OPTICALLY-ACTIVE VITAMIN-E C-14 SIDE-CHAIN ALCOHOL [J].

BERUBE, G ;

DESLONGCHAMPS, P .

CANADIAN JOURNAL OF CHEMISTRY, 1984, 62 (08) :1558-1560

[3]

BERUBE G, 1987, B SOC CHIM FR, P103

[4] PHYTENE-1,2-DIOL FROM ARTEMISIA-ANNUA [J].

BROWN, GD .

PHYTOCHEMISTRY, 1994, 36 (06) :1553-1554

[5] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[6] ISOLATION OF RACEMIC 2,4-PENTANEDIOL AND 2,5-HEXANEDIOL FROM COMMERCIAL MIXTURES OF RACEMIC AND MESO ISOMERS BY WAY OF CYCLIC SULFITES [J].

CARON, G ;

KAZLAUSKAS, RJ .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :657-664

[7]

CHESKIS BA, 1988, IAN SSSR KH, V4, P865

[8] NOVEL TOTAL SYNTHESIS OF (2R,4'R,8'R)-ALPHA-TOCOPHEROL (VITAMIN-E) - CONSTRUCTION OF CHIRAL CHROMANS FROM AN OPTICALLY-ACTIVE, NON-AROMATIC PRECURSOR [J].

COHEN, N ;

LOPRESTI, RJ ;

SAUCY, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (22) :6710-6716

[9] SYNTHETIC STUDIES ON 2R,4',8'R-ALPHA-TOCOPHEROL - APPROACH UTILIZING SIDE-CHAIN SYNTHONS OF MICROBIOLOGICAL ORIGIN [J].

COHEN, N ;

EICHEL, WF ;

LOPRESTI, RJ ;

NEUKOM, C ;

SAUCY, G .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3505-3511

[10] SYNTHESIS OF (2RS,4'R,8'R)-ALPHA-TOCOPHEROL AND RELATED-COMPOUNDS VIA A 2-CHLOROCHROMAN [J].

COHEN, N ;

SCHAER, B ;

SCALONE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5783-5785

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