Synthesis of α-alkylidene-β-ethoxycarbonyl cyclopentanones and -γ-butyrolactones

被引:16
作者
Beji, F [1 ]
Besbes, R [1 ]
Amri, H [1 ]
机构
[1] Fac Sci, Lab Chim Organ & Organomet, Tunis 1060, Tunisia
关键词
D O I
10.1080/00397910008086954
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of (E,Z)-alpha-Alkylidene-beta-ethoxycarbonyl cyclopentanones 5 and(E,Z)-alpha-alkylidene-gamma-butyrolactones 7 by condensing phosphonates 3 or 6 with a variety of aldehydes in the presence of aqueous potassium carbonate (6-10M) as base is reported.
引用
收藏
页码:3947 / 3954
页数:8
相关论文
共 12 条
[1]   A SHORT LARGE-SCALE SYNTHESIS OF (+/-)SARKOMYCIN ESTERS [J].
AMRI, H ;
RAMBAUD, M ;
VILLIERAS, J .
TETRAHEDRON LETTERS, 1989, 30 (52) :7381-7382
[2]   ARBUZOV-LIKE DEALKYLATION REACTIONS OF TRANSITION-METAL PHOSPHITE COMPLEXES [J].
BRILL, TB ;
LANDON, SJ .
CHEMICAL REVIEWS, 1984, 84 (06) :577-585
[3]  
CAMPAIGNE E, 1978, SYNTHESIS-STUTTGART, P385
[4]  
GARIN J, 1983, SYNTHESIS-STUTTGART, P406
[5]   ALPHA-CARBOXYLATION OF LACTONES - GENERAL ROUTE TO ALPHA-METHYLENE LACTONES [J].
GRIECO, PA ;
HIROI, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (14) :500-501
[6]   REGEL ZUR ABSCHATZUNG DER CHEMISCHEN VERSCHIEBUNG VON PROTONEN AN EINER DOPPELBINDUNG [J].
PASCUAL, C ;
MEIER, J ;
SIMON, W .
HELVETICA CHIMICA ACTA, 1966, 49 :164-&
[7]  
PIECHUCKI C, 1974, SYNTHESIS-STUTTGART, P869
[8]  
PIECHUKI C, 1974, SYNTHESIS-STUTTGART, P178
[9]   STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-XANTHOCIDIN, 2 DIASTEREOMERS, (+/-)-EPIXANTHOCIDIN AND (+/-)-BETA-ISOXANTHOCIDIN, AND (+/-)-DESDIHYDROXY-4,5-DIDEHYDROXANTHOCIDIN, A LIKELY BIOSYNTHETIC PRECURSOR [J].
SMITH, AB ;
BOSCHELLI, D .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) :1217-1226
[10]   THE WITTIG-HORNER REACTION IN HETEROGENOUS ENVIRONMENT VI1 - SELECTIVITY OF THE REACTION ON BIFUNCTIONAL COMPOUNDS [J].
VILLIERAS, J ;
RAMBAUD, M ;
GRAFF, M .
TETRAHEDRON LETTERS, 1985, 26 (01) :53-56