SYNTHESIS OF METHYL 5-HYDROXY-2METHYL-3-OXO-1-CYCLOPENTENE-1-CARBOXYLATE - METHYL ESTER OF A PICROTOXININ DEGRADATION PRODUCT

被引:9
作者
FINCH, N
SCHLITTLER, E
机构
[1] Chemical Research Division, CIBA Pharmaceutical Company, Division of CIBA Corporation, Summit, NJ
关键词
D O I
10.1016/S0040-4020(01)96336-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The known methyl 2-methyl-3-oxo-1-cyclopentene carboxylate was acetoxylated by reaction with N-bromosuccinimide and subsequent treatment with silver acetate. Methanolysis of this acetoxy compound yielded methyl 5-hydroxy-2-methyl-3-oxo-1-cyclopentene carboxylate. Reaction of silver 3,5-dinitrobenzoate with the intermediate bromo compound yielded the corresponding 3,5-dinitrobenzoate, which was identical with that derived from a picrotoxinin degradation product. © 1968.
引用
收藏
页码:5421 / +
页数:1
相关论文
共 16 条
[1]   REACTION OF ACETYLENIC ESTERS WITH CYANOACETIC ESTER AND PYRIDINE [J].
BAMFIELD, P ;
CRABTREE, A ;
JOHNSON, AW .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (AUG) :4355-&
[4]  
CONROY H, 1951, J AM CHEM SOC, V73, P1889, DOI 10.1021/ja01148a552
[5]  
CRAVEN BM, 1960, TETRAHEDRON LETT, P21
[6]   CRYSTAL STRUCTURE OF ALPHA1-BROMOPICROTOXININ [J].
CRAVEN, BM .
ACTA CRYSTALLOGRAPHICA, 1962, 15 (APR) :387-&
[7]   FORMATION OF CYCLOPENTADIENONES [J].
DEPUY, CH ;
ISAKS, M ;
MORRIS, GF ;
EILERS, KL .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (12) :3503-&
[8]  
ESPLIN DW, 1965, PHARMACOL BASIS, P348
[9]  
GOODMAN LS, 1965, PHARMACOLOGICAL B ED, P348
[10]   PICROTOXIN AND TUTIN .8. [J].
JOHNS, RB ;
SLATER, SN ;
WOODS, RJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (DEC) :4715-4727