USE OF CIS-3-CYCLOBUTENE-1,2-DIMETHANOL IN STEREOSELECTIVE ROUTES TO SOME NATURALLY-OCCURRING CONJUGATED DIENES AND TRIENES

被引:11
作者
HODGETTS, KJ
SAENGCHANTARA, ST
WALLIS, CJ
WALLACE, TW
机构
[1] UNIV SALFORD,DEPT CHEM & APPL CHEM,SALFORD M5 4WT,LANCS,ENGLAND
[2] GLAXO GRP RES LTD,WARE SG12 0DP,HERTS,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)73742-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thermal electrocyclic ring-opening of 4-alkyl-2-cyclobutene-1-carbaldehydes occurs at low temperature to give (2Z,4E)-alka-2,4-dienals exclusively, and this process is exploited en route to various isomeric naturally occurring 1,3,5-alkatrienes and 2,4-decadienoates from a single precursor, cis-3-cyclobutene-1,2-dimethanol 4.
引用
收藏
页码:6321 / 6324
页数:4
相关论文
共 35 条
[1]   SYNTHESIS AND CHARACTERIZATION OF ALL 4 ISOMERS OF METHYL 2,4-DECADIENOATE FOR AN INVESTIGATION OF THE PHEROMONE COMPONENTS OF PITYOGENES-CHALCOGRAPHUS [J].
BAECKSTROM, P ;
JACOBSSON, U ;
NORIN, T ;
UNELIUS, CR .
TETRAHEDRON, 1988, 44 (09) :2541-2548
[2]   THERMAL ELECTROCYCLIC RING-OPENING OF CYCLOBUTENES - STEREOSELECTIVE ROUTES TO FUNCTIONALIZED CONJUGATED (Z,E)-DIENES AND (E,E)-2,4-DIENALS [J].
BINNS, F ;
HAYES, R ;
INGHAM, S ;
SAENGCHANTARA, ST ;
TURNER, RW ;
WALLACE, TW .
TETRAHEDRON, 1992, 48 (03) :515-530
[3]   ACID-BASE CONTROLLED TORQUOSELECTIVITY - THEORETICAL PREDICTIONS OF THE STEREOCHEMICAL COURSE OF THE ELECTROCYCLIC REACTIONS OF CYCLOBUTENE-3-CARBOXYLIC ACID AND THE CONJUGATE BASE AND ACID [J].
BUDA, AB ;
WANG, Y ;
HOUK, KN .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2264-2266
[4]   A SIMPLE STEREOSELECTIVE SYNTHESIS OF GALBANOLENE, (3E,5Z)-1,3,5-UNDECATRIENE [J].
CHAPUIS, C .
TETRAHEDRON LETTERS, 1992, 33 (18) :2461-2464
[5]  
CHRETIEN.Y, 1967, B SOC CHIM FR, P97
[6]  
COLLINGT.EW, 1971, J ORG CHEM, V36, P3044
[7]   NEW METHODS FOR OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS AND ESTERS [J].
COREY, EJ ;
GILMAN, NW ;
GANEM, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5616-&
[8]   AMIDES OF VEGETABLE ORIGIN .5. STEREOCHEMISTRY OF CONJUGATED DIENES [J].
CROMBIE, L .
JOURNAL OF THE CHEMICAL SOCIETY, 1955, :1007-1025
[9]   A NEW 2-CARBON OLEFIN HOMOLOGATION PROCEDURE THAT LEADS TO ALPHA-CHLOROENONES - AN EFFICIENT SYNTHESIS OF D,L-MUSCONE [J].
DEPRES, JP ;
NAVARRO, B ;
GREENE, AE .
TETRAHEDRON, 1989, 45 (10) :2989-2998
[10]   NEW TRIENE SYNTHESIS FROM SORBIC ACID - 2-STEP SYNTHESIS OF CIS-GALBANOLENES AND TRANS-GALBANOLENES [J].
FEHR, C ;
GALINDO, J ;
CHAPPUIS, S .
TETRAHEDRON LETTERS, 1992, 33 (18) :2465-2468