CONSTRUCTION OF ALPHA-ALKYLIDENE-GAMMA-BUTYROLACTONES FROM ACYCLIC ESTER PRECURSORS

被引：22

作者：

LU, XY

MA, SM

JI, JG

ZHU, GX

JIANG, HF

机构：

[1] Shanghai Institute of Organic Chemistry, Academia Sinica, 345 Lingling Lu

来源：

PURE AND APPLIED CHEMISTRY | 1994年 / 66卷 / 07期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1351/pac199466071501

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Divalent palladium catalyzed cyclization of allylic alkynoates were studied. Alpha-Alkylidene-gamma-butyrolactones were produced highly regio- and stereoselectively. Controlling factors on the stereochemistry of exocyclic double bonds and beta,gamma-substituents were carefully studied. Bicyclic alpha-alkylidene-gamma-lactones were also synthesized using this method. A convenient and potentially useful methodology is provided for the synthesis of natural products.

引用

收藏

页码：1501 / 1508

页数：8

相关论文

共 45 条

[1] PALLADIUM-CATALYZED OXIDATIVE CYCLIZATION OF 1,5-DIENES - INFLUENCE OF DIFFERENT SUBSTITUTION PATTERNS ON THE REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE REACTION [J].

ANTONSSON, T ;

MOBERG, C ;

TOTTIE, L ;

HEUMANN, A .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4914-4929

[2] SYNTHESIS OF ALPHA-ALKYLIDENE-GAMMA-LACTONES BY INTRAMOLECULAR ADDITION OF ALKOXYCARBONYL FREE-RADICALS TO ACETYLENES [J].

BACHI, MD ;

BOSCH, E .

TETRAHEDRON LETTERS, 1986, 27 (05) :641-644

[3]

BACKVALL JE, 1977, TETRAHEDRON LETT, P467

[4] STEREOCHEMISTRY OF HYDROXYPALLADATION STEP IN WACKER PROCESS [J].

BACKVALL, JE ;

AKERMARK, B ;

LJUNGGREN, SO .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (08) :264-265

[5] CHEMISTRY AND SYNTHESIS OF LIGNAN(-)-CUBEBIN [J].

BATTERBEE, JE ;

BURDEN, RS ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18) :2470-+

[6]

GRIECO PA, 1975, SYNTHESIS-STUTTGART, P67

[7] IODOVINYLIDENE LACTONE SYNTHESIS - FREE-RADICAL CYCLIZATION OF IODO ACETYLENIC ESTERS [J].

HAAIMA, G ;

WEAVERS, RT .

TETRAHEDRON LETTERS, 1988, 29 (09) :1085-1088

[8] CARBON OXYGEN BOND-CLEAVAGE OF ESTERS PROMOTED BY HYDRIDO AND ALKYLCOBALT(I) COMPLEXES HAVING TRIPHENYLPHOSPHINE LIGANDS - ISOLATION OF AN INSERTION INTERMEDIATE AND MOLECULAR-STRUCTURE OF PHENOXOTRIS(TRIPHENYLPHOSPHINE)COBALT(I) [J].

HAYASHI, Y ;

YAMAMOTO, T ;

YAMAMOTO, A ;

KOMIYA, S ;

KUSHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (03) :385-391

[9] NEW APPLICATIONS OF PALLADIUM IN ORGANIC SYNTHESES [J].

HECK, RF .

PURE AND APPLIED CHEMISTRY, 1978, 50 (08) :691-701

[10] SYNTHESIS OF UNSATURATED BUTYROLACTONES BY PALLADIUM CATALYZED INTRAMOLECULAR CARBOALKOXYLATION OF HOMOALLYLIC CHLOROFORMATES [J].

HENIN, F ;

PETE, JP .

TETRAHEDRON LETTERS, 1983, 24 (43) :4687-4690

← 1 2 3 4 5 →