SEX-PHEROMONE OF PINE SAWFLIES - CHIRAL SYNTHESES OF SOME ACTIVE MINOR COMPONENTS ISOLATED FROM NEODIPRION-SERTIFER AND OF SOME CHIRAL ANALOGS OF DIPRIONYL ACETATE

被引：38

作者：

HEDENSTROM, E

HOGBERG, HE

WASSGREN, AB

BERGSTROM, G

LOFQVIST, J

HANSSON, B

ANDERBRANT, O

机构：

[1] UNIV GOTEBORG,DEPT CHEM ECOL,S-41320 GOTHENBURG,SWEDEN

[2] UNIV LUND,DEPT ECOL,S-22362 LUND,SWEDEN

来源：

TETRAHEDRON | 1992年 / 48卷 / 15期

关键词：

CHIRAL SYNTHESIS; PHEROMONE; NEODIPRION-SERTIFER; DIPRIONOL;

D O I：

10.1016/S0040-4020(01)92255-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral syntheses of some analogues, 2 - 7, of 3,7-dimethyl-2-pentadecanol, 1 (diprionol), and of the corresponding acetates are described. The acetate of 1 is the main attractant in the sex pheromone of the Neodiprion genus (Diprionidae). Compounds 2 - 4 were identified as minor components isolated from females of Neodiprion sertifer. Synthetic intermediates were prepared either from chiral starting materials, via asymmetric syntheses, or by baker's yeast reductions.

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页码：3139 / 3146

页数：8

相关论文

共 25 条

[1] TRANS-PERILLENAL - FURANOID MONOTERPENE FROM PINE SAW-FLY, NEODIPRION-SERTIFER (HYMENOPTERA, DIPRIONIDAE) [J].

AHLGREN, G ;

BERGSTROM, G ;

LOFQVIST, J ;

JANSSON, A ;

NORIN, T .

JOURNAL OF CHEMICAL ECOLOGY, 1979, 5 (03) :309-319

[2] EFFECTS OF PHEROMONE TRAP TYPE, POSITION AND COLOR ON THE CATCH OF THE PINE SAWFLY NEODIPRION-SERTIFER (GEOFF) (HYM, DIPRIONIDAE) [J].

ANDERBRANT, O ;

LOFQVIST, J ;

JONSSON, J ;

MARLING, E .

JOURNAL OF APPLIED ENTOMOLOGY-ZEITSCHRIFT FUR ANGEWANDTE ENTOMOLOGIE, 1989, 107 (04) :365-369

[3]

ANDERBRANT O, 1992, IN PRESS ENT EXP APP, V46

[4]

BAECKSTROM P, 1982, ACTA CHEM SCAND B, V36, P31

[5]

BOECKSTROM P, 1987, ACTA CHEM SCAND B, V41, P442

[6] CHIRAL SYNTHESIS OF (2S,3S,7S)-3,7-DIMETHYLPENTADECAN-2-YL ACETATE AND PROPIONATE, POTENTIAL SEX-PHEROMONE COMPONENTS OF THE PINE SAW-FLY NEODIPRION-SERTIFER (GEOFF) [J].

BYSTROM, S ;

HOGBERG, HE ;

NORIN, T .

TETRAHEDRON, 1981, 37 (12) :2249-2254

[7] BAKERS-YEAST MEDIATED PREPARATION OF (S)-3-(2-FURYL)-2-METHYLPROPAN-1-OL, A BIFUNCTIONAL CHIRAL-C-S ISOPRENOID SYNTHON - SYNTHESIS OF (4R,8R)-4,8-DIMETHYLDECANAL, A PHEROMONE OF TRIBOLIUM-CASTANEUM [J].

FUGANTI, C ;

GRASSELLI, P ;

SERVI, S ;

HOGBERG, HE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3061-3065

[8] MORPHOLOGY AND ULTRASTRUCTURE OF AN INTERTERGAL PHEROMONE GLAND IN THE ABDOMEN OF THE PINE SAWFLY NEODIPRION-SERTIFER (INSECTA, HYMENOPTERA) - A POTENTIAL SOURCE OF SEX-PHEROMONES [J].

HALLBERG, E ;

LOFQVIST, J .

CANADIAN JOURNAL OF ZOOLOGY, 1981, 59 (01) :47-53

[9] SEX-PHEROMONE PERCEPTION IN MALE PINE SAWFLIES, NEODIPRION-SERTIFER (HYMENOPTERA, DIPRIONIDAE) [J].

HANSSON, BS ;

VANDERPERS, JNC ;

HOGBERG, HE ;

HEDENSTROM, E ;

ANDERBRANT, O ;

LOFQVIST, J .

JOURNAL OF COMPARATIVE PHYSIOLOGY A-NEUROETHOLOGY SENSORY NEURAL AND BEHAVIORAL PHYSIOLOGY, 1991, 168 (05) :533-538

[10] SYNTHESIS AND GAS-CHROMATOGRAPHIC SEPARATION OF THE 8 STEREOISOMERS OF DIPRIONOL AND THEIR ACETATES, COMPONENTS OF THE SEX-PHEROMONE OF PINE SAWFLIES [J].

HOGBERG, HE ;

HEDENSTROM, E ;

WASSGREN, AB ;

HJALMARSSON, M ;

BERGSTROM, G ;

LOFQVIST, J ;

NORIN, T .

TETRAHEDRON, 1990, 46 (08) :3007-3018