Improved synthesis of methyl 7,7-ethylenedioxy-3-methyl-9-oxobicyclo[3.3.1]non-3-ene-1-carboxylate, intermediate for the synthesis of Huperzine A analogues

被引：8

作者：

Camps, P ^{[1
]}

Contreras, J ^{[1
]}

FontBardia, M ^{[1
]}

Solans, X ^{[1
]}

机构：

[1] UNIV BARCELONA, FAC GEOL, DEPT CRISTALLOG MINERAL & DIPOSITS MINERALS, E-08028 BARCELONA, SPAIN

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 01期

关键词：

D O I：

10.1080/00397919608003857

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound 4 has been obtained in an improved yield, from 1 via alcohol 2a, which was dehydrated by pyrolytic syn-elimination of its derived thiocarbonate 2c. A trans-configuration of 2a and its stereoisomer 3a was established by X-ray diffraction analysis of their mesylates 2b and 3b.

引用

页码：9 / 18

页数：10

共 23 条

[1] SYNTHESIS AND EVALUATION OF TACRINE-RELATED COMPOUNDS FOR THE TREATMENT OF ALZHEIMERS-DISEASE [J].

AGUADO, F ;

BADIA, A ;

BANOS, JE ;

BOSCH, F ;

BOZZO, C ;

CAMPS, P ;

CONTRERAS, J ;

DIERSSEN, M ;

ESCOLANO, C ;

GORBIG, DM ;

MUNOZTORRERO, D ;

PUJOL, MD ;

SIMON, M ;

VAZQUEZ, MT ;

VIVAS, NM .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (03) :205-221

[2]

[Anonymous], INT TABLES XRAY CRYS

[3] CONFORMATIONAL-ANALYSIS, SYNTHESIS, AND C-13 SPECTROSCOPY OF 9,9-DIMETHYLBICYCLO[3.3.1]NONANE DERIVATIVES [J].

ARANDA, G ;

BERNASSAU, JM ;

FETIZON, M ;

HANNA, I .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1156-1161

[4] A PALLADIUM-CATALYZED ROUTE TO HUPERZINE-A AND ITS ANALOGS AND THEIR ANTICHOLINESTERASE ACTIVITY [J].

CAMPIANI, G ;

SUN, LQ ;

KOZIKOWSKI, AP ;

AAGAARD, P ;

MCKINNEY, M .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7660-7669

[5] CONFORMATION OF TRICYCLE [4.3.1.1(2,5)]UNDEC-3-EN-10-ONE [J].

CAMPS, P ;

VAZQUEZ, S ;

JAIME, C ;

VIRGILI, A .

MAGNETIC RESONANCE IN CHEMISTRY, 1994, 32 (04) :210-212

[6]

HE XC, 1993, CHINESE CHEM LETT, V4, P597

[7]

HE XC, 1994, CHINESE CHEM LETT, V5, P471

[8] SYNTHESIS AND ACETYLCHOLINESTERASE INHIBITORY ACTIVITY OF SEVERAL PYRIMIDONE ANALOGS OF HUPERZINE-A [J].

KOZIKOWSKI, AP ;

CAMPIANI, G ;

SAXENA, A ;

DOCTOR, BP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :283-285

[9]

KOZIKOWSKI AP, 1994, HETEROCYCLES, V39, P101

[10] SYNTHESIS AND BIOLOGICAL EVALUATION OF (+/-)-Z-HUPERZINE-A [J].

KOZIKOWSKI, AP ;

YAMADA, F ;

TANG, XC ;

HANIN, I .

TETRAHEDRON LETTERS, 1990, 31 (43) :6159-6162

← 1 2 3 →