SYNTHESES OF ALL-TRANS ACYCLIC ISOPRENOID PHEROMONE COMPONENTS

被引:8
作者
BAECKSTROM, P
LI, L
机构
[1] Department of Organic Chemistry, Royal Institute of Technology
关键词
D O I
10.1016/S0040-4020(01)86580-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
All-trans acyclic isoprenoid skeletons were made through a two-step iterative sequence. The method involves the Claisen rearrangement of allyl vinyl ethers formed from allylic alcohols and the dimethyl acetal of methyl isopropenyl ketone, followed by LiAlH4 reduction of the alpha,beta-unsaturated ketone formed by rearrangement. The alpha,beta-unsaturated ketone was also transformed to the 2-methyl-1-propenyl group by using a one-pot deoxygenation reaction for the synthesis of (E)-beta-farnesene, (E)-beta-springene and dendrolasin.
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页码:6533 / 6538
页数:6
相关论文
共 23 条
[1]  
ADUSUMILLI S, 1988, CHEM LETT, P371
[2]   A ONE POT PROCEDURE FOR THE DEOXYGENATION OF ALPHA,BETA-UNSATURATED KETONES AND A SYNTHESIS OF THE MEALYBUG PHEROMONE [J].
BAECKSTROM, P ;
LI, L .
SYNTHETIC COMMUNICATIONS, 1990, 20 (10) :1481-1485
[3]   A SYNTHESIS OF TRANS-BETA-FARNESENE FROM MYRCENE WHICH INCLUDES A MODIFIED WORK UP METHOD FOR DIBAH REDUCTIONS OF ESTERS TO ALDEHYDES [J].
BAECKSTROM, P ;
LI, L ;
WICKRAMARATNE, M ;
NORIN, T .
SYNTHETIC COMMUNICATIONS, 1990, 20 (03) :423-429
[4]  
BAECKSTROM P, 1982, ACTA CHEM SCAND B, V36, P31
[5]   CLAISEN REARRANGEMENTS WITH MESITYL OXIDE DIMETHYL KETAL - SYNTHESIS OF IPSDIENONE, E-OCIMENONE, AND Z-OCIMENONE, 2,6-DIMETHYL-2,7-OCTADIEN-4-ONE AND 2,6-DIMETHYL-2,7-OCTADIEN-4-OL [J].
BAECKSTROM, P ;
STRIDH, K ;
LI, L ;
NORIN, T .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1987, 41 (06) :442-447
[6]  
BAECKSTROM P, UNPUB
[7]   APHID ALARM PHEROMONE - ISOLATION, IDENTIFICATION, SYNTHESIS [J].
BOWERS, WS ;
WEBB, RE ;
NAULT, LR ;
DUTKY, SR .
SCIENCE, 1972, 177 (4054) :1121-&
[8]  
BURGER BV, 1978, TETRAHEDRON LETT, P5221
[9]   PREPARATION AND PROPERTIES OF A SERIES OF ALKYL-4,4-DIMETHYLCYCLOHEXA 2,5-DIENONES, AND RELATED CYCLOHEXENONES AND CYCLOHEXANONES [J].
COOK, KL ;
WARING, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (05) :529-537
[10]   IMPROVED PREPARATION OF (E)-BETA-FARNESENE AND ITS ACTIVITY WITH ECONOMICALLY IMPORTANT APHIDS [J].
DAWSON, GW ;
GRIFFITHS, DC ;
PICKETT, JA ;
SMITH, MC ;
WOODCOCK, CM .
JOURNAL OF CHEMICAL ECOLOGY, 1982, 8 (08) :1111-1117