DIELS-ALDER REACTIONS OF TRANS-1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE

被引:202
作者
DANISHEFSKY, S
KITAHARA, T
YAN, CF
MORRIS, J
机构
[1] Contribution from the Department of Chemistry, University of Pittsburgh, 15260, Pittsburgh, Pennsylvania
关键词
D O I
10.1021/ja00517a036
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enol silylation of trans-4-methoxybut-3-en-2-one affords trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene (1). This compound has been demonstrated to be a valuable diene in Diels-Alder reactions. These processes provide new and effective routes to aromatic and cyclohexenone systems. The pathways by which the intermediate 3-methoxy-l-silyloxycyclohexenes are transformed to cyclohexenones are considered. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:6996 / 7000
页数:5
相关论文
共 64 条
[1]   DIHYDROAROMATIC COMPOUNDS IN DIELS-ALDER REACTION .3. IN-SITU GENERATION AND DIELS ALDER REACTION OF CYCLOHEXA-1,3-DIENES [J].
ALFARO, I ;
ASHTON, W ;
MCMANUS, LD ;
NEWSTEAD, RC ;
RABONE, KL ;
KERNICK, W .
TETRAHEDRON, 1970, 26 (01) :201-&
[2]   4-Hydroxyphthalic and 4-methoxyphthalic acids [J].
Bentley, WH ;
Weizmann, C .
JOURNAL OF THE CHEMICAL SOCIETY, 1907, 91 :98-104
[3]  
BOZOUIN A, 1966, Patent No. 1436568
[4]  
CAZEAU P, 1972, B SOC CHIM FR, P1658
[5]   SILICON IN ORGANIC-SYNTHESIS [J].
COLVIN, EW .
CHEMICAL SOCIETY REVIEWS, 1978, 7 (01) :15-64
[6]   NEW SYNTHESIS OF CONJUGATED NITRO CYCLO OLEFINS, UNUSUALLY VERSATILE SYNTHETIC INTERMEDIATES [J].
COREY, EJ ;
ESTREICHER, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (19) :6294-6295
[7]  
COREY EJ, 1978, J AM CHEM SOC, V100, P8034, DOI 10.1021/ja00493a056
[8]   SYNTHESIS OF DISODIUM PREPHENATE AND DISODIUM EPIPREPHENATE - STEREOCHEMISTRY OF PREPHENIC ACID AND AN OBSERVATION ON THE BASE-CATALYZED REARRANGEMENT OF PREPHENIC ACID TO PARA-HYDROXYPHENYLLACTIC ACID [J].
DANISHEFSKY, S ;
HIRAMA, M ;
FRITSCH, N ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7013-7018
[9]   STEREOSPECIFIC SYNTHESIS OF GRISEOFULVIN [J].
DANISHEFSKY, S ;
WALKER, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7018-7020
[10]   TOTAL SYNTHESIS OF DL-PENTALENOLACTONE [J].
DANISHEFSKY, S ;
HIRAMA, M ;
GOMBATZ, K ;
HARAYAMA, T ;
BERMAN, E ;
SCHUDA, PF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7020-7031