SYNTHESIS OF CHIRAL ALCOHOL AND ESTER PHEROMONES THROUGH ENZYME-CATALYZED HYDROLYSIS USING PSEUDOMONAS-FLUORESCENS LIPASE - PREPARATION OF (2R,6S,10S)-6,10-14-TRIMETHYLPENTADECAN-2-OL AND THE PROPIONATE OF (2R,8R)-8-METHYLDECAN-2-OL

被引：21

作者：

NAOSHIMA, Y

MUNAKATA, Y

YOSHIDA, S

FUNAI, A

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 03期

关键词：

D O I：

10.1039/p19910000549

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2R, 6S, 10S)-6, 10, 14-Trimethylpentadecan-2-ol [(2R,6S,10S)-5], one of the stereoisomers of the sex pheromone of Corcyra cephalonica Stainton, was synthesized in highly optically pure form by the hydrolysis of the 2,2,2-trichloroethyl carbonate of (2R,6S,10S)-6, 10, 14-trimethylpentadecan-2-ol [(2RS, 6S, 10S)-15a] with Pseudomonas fluorescens lipase. The same method led to sterochemically pure (2R,8R)-8-methyldecan-2-yl propionate [(2R,8R)-24], which is a component of the sex pheromone of Diabrotica species.

引用

收藏

页码：549 / 553

页数：5

相关论文

共 22 条

[1]

ABRAMOWICZ DA, 1990, BIOCATALYST

[2] SYNTHETIC STUDIES ON (2R,4'R,8'R)-ALPHA-TOCOPHEROL FACILE SYNTHESES OF OPTICALLY-ACTIVE, SATURATED, ACYCLIC ISOPRENOIDS VIA STEREOSPECIFIC [3,3] SIGMATROPIC REARRANGEMENTS [J].

CHAN, KK ;

COHEN, N ;

DENOBLE, JP ;

SPECIAN, AC ;

SAUCY, G .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3497-3505

[3]

Davies H.G., 1989, BIOTRANSFORMATION PR

[4] IDENTIFICATION OF A FEMALE-PRODUCED SEX-PHEROMONE OF THE WESTERN CORN-ROOTWORM [J].

GUSS, PL ;

TUMLINSON, JH ;

SONNET, PE ;

PROVEAUX, AT .

JOURNAL OF CHEMICAL ECOLOGY, 1982, 8 (02) :545-556

[5] RESPONSE OF DIABROTICA-VIRGIFERA-VIRGIFERA, DIABROTICA-VIRGIFFERA-ZEAE, (COLEOPTERA, CHRYSOMELIDAE) AND DIABROTICA-PORRACEA (COLEOPTERA, CHRYSOMELIDAE) TO STEREOISOMERS OF 8-METHYL-2-DECYL PROPANOATE [J].

GUSS, PL ;

SONNET, PE ;

CARNEY, RL ;

BRANSON, TF ;

TUMLINSON, JH .

JOURNAL OF CHEMICAL ECOLOGY, 1984, 10 (07) :1123-1131

[6] RESPONSE OF NORTHERN CORN-ROOTWORM, DIABROTICA-BARBERI SMITH AND LAWRENCE, (COLEOPTERA, CHRYSOMEUDAE) TO STEREOISOMERS OF 8-METHYL-2-DECYL PROPANOATE [J].

GUSS, PL ;

SONNET, PE ;

CARNEY, RL ;

TUMLINSON, JH ;

WILKIN, PJ .

JOURNAL OF CHEMICAL ECOLOGY, 1985, 11 (01) :21-26

[7] SEX-PHEROMONES OF RICE MOTH, CORCYRA-CEPHALONICA STAINTON .2. IDENTIFICATION AND ROLE OF FEMALE PHEROMONE [J].

HALL, DR ;

CORK, A ;

LESTER, R ;

NESBITT, BF ;

ZAGATTI, P .

JOURNAL OF CHEMICAL ECOLOGY, 1987, 13 (07) :1575-1589

[8] PHEROMONE SYNTHESIS .60. SYNTHESIS OF THE PROPIONATES OF (2R, 8R)-8-METHYL-2-DECANOL AND (2S, 8R)-8-METHYL-2-DECANOL, THE PHEROMONE OF THE WESTERN CORN-ROOTWORM, EMPLOYING CHIRAL COMPOUNDS OF MICROBIAL ORIGIN AS STARTING MATERIALS [J].

MORI, K ;

WATANABE, H .

TETRAHEDRON, 1984, 40 (02) :299-303

[9] SYNTHETIC MICROBIAL CHEMISTRY .3. REVISION OF THE ABSOLUTE-CONFIGURATION OF A-FACTOR - THE INDUCER OF STREPTOMYCIN BIOSYNTHESIS, BASING ON THE RECONFIRMED (R)-CONFIGURATION OF (+)-PARACONIC ACID [J].

MORI, K .

TETRAHEDRON, 1983, 39 (19) :3107-3109

[10] BIOTRANSFORMATION OF SOME KETO ESTERS THROUGH THE CONSECUTIVE REUSE OF IMMOBILIZED NICOTIANA-TABACUM CELLS [J].

NAOSHIMA, Y ;

AKAKABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4237-4239