PRACTICAL PREPARATION OF BICYCLO[3.2.0]HEPT-3-EN-6-ONES AND IT UTILIZATION IN STEREOSELECTIVE TOTAL SYNTHESIS OF GRANDISOL AND LINEATIN VIA A VERSATILE INTERMEDIATE

被引：28

作者：

CONFALONIERI, G

MAROTTA, E

RAMA, F

RIGHI, P

ROSINI, G

SERRA, R

VENTURELLI, F

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM ORGAN A MANGINI,I-40136 BOLOGNA,ITALY

[2] ISAGRO SRL,RIC FITOFARM,ENICHEM,I-28100 NOVARA,ITALY

来源：

TETRAHEDRON | 1994年 / 50卷 / 10期

关键词：

D O I：

10.1016/S0040-4020(01)81119-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New and efficient stereoselective total syntheses have been devised for racemic grandisol and lineatin, two important components of pheromonic blends. They are based on the utilisation of 1,4-dimethylbicyclo[3.2.0]hept-3-en-6-one as a pivotal intermediate. This compound, as well as other bicyclo[3.2.0]hept-3-en-6-ones, are now easily available by a practical bicyclization of the corresponding 3-hydroxy-6-alkenoic acids.

引用

页码：3235 / 3250

页数：16

共 59 条

[11] CAMPION DG, 1984, TECHNIQUES PHEROMONE
[12] A SYNTHESIS OF HOMOALLYLIC ALCOHOLS
CRANDALL, JK
BANKS, DB
COLYER, RA
WATKINS, RJ
ARRINGTO.JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) : 423 - &
[13] RECEPTOR CHIRALITY AND BEHAVIORAL SPECIFICITY OF THE BOLL-WEEVIL, ANTHONOMUS-GRANDIS BOH (COLEOPTERA, CURCULIONIDAE), FOR ITS PHEROMONE, (+)-GRANDISOL
DICKENS, JC
MORI, K
[J]. JOURNAL OF CHEMICAL ECOLOGY, 1989, 15 (02) : 517 - 528
[14] FLEMING I, 1975, CHEM IND-LONDON, P449
[15] Francke W., 1986, Advances in Invertebrate Reproduction, V4, P327
[16] TERPENOIDS FROM BARK BEETLES, SOLITARY BEES AND DANAINE BUTTERFLIES
FRANCKE, W
BARTELS, J
KROHN, S
SCHULZ, S
BAADER, E
TENGO, J
SCHNEIDER, D
[J]. PURE AND APPLIED CHEMISTRY, 1989, 61 (03) : 539 - 542
[17] REACTION OF KETENE IMINIUM IONS WITH DIFFERENT OLEFINS - NOVEL PREPARATION OF (+/-)-GRANDISOL, (+/-)-FRAGRANOL AND CORRESPONDING METHYL ETHERS
GRANDGUILLOT, JC
ROUESSAC, F
[J]. TETRAHEDRON, 1991, 47 (28) : 5133 - 5148
[18] C(12)-SUBSTITUTED PROSTAGLANDINS - AN ENANTIOSPECIFIC TOTAL SYNTHESIS OF (+)-12-(FLUOROMETHYL)PROSTAGLANDIN-F2-ALPHA METHYL-ESTER
GRIECO, PA
VEDANANDA, TR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) : 3497 - 3502
[19] Griffith W. P., 1990, ALDRICHIM ACTA, V23, P13
[20] PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS
GRIFFITH, WP
LEY, SV
WHITCOMBE, GP
WHITE, AD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) : 1625 - 1627

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