TOTAL SYNTHESIS OF AN OPTICALLY-ACTIVE 8-CARBA-PHYSOSTIGMINE ANALOG - A POTENT ACETYLCHOLINESTERASE INHIBITOR

被引：8

作者：

CHEN, YL

HEDBERG, K

机构：

[1] Central Research Division, Pfizer Inc, Groton

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1991年 / 1卷 / 01期

关键词：

D O I：

10.1016/S0960-894X(01)81088-X

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Syntheses of 8-carba-physostigmine enantiomers 2a and 2b via optically active intermediates 9a and 9b are described. The key synthetic intermediate 9 was prepared via a [2 + 2] cycloaddition of indene 4 and dichloroketene, followed by Beckmann rearrangement, reduction and resolution.

引用

收藏

页码：47 / 50

页数：4

相关论文

共 10 条

[1]

BRADY WT, 1981, TETRAHEDRON, V37, P2949

[2] PHYSOSTIGMINE AND ARECOLINE - EFFECTS OF INTRAVENOUS INFUSIONS IN ALZHEIMER PRESENILE-DEMENTIA [J].

CHRISTIE, JE ;

SHERING, A ;

FERGUSON, J ;

GLEN, AIM .

BRITISH JOURNAL OF PSYCHIATRY, 1981, 138 (JAN) :46-50

[3]

DAVIS KL, 1982, AM J PSYCHIAT, V139, P1421

[4]

GIBSON M, 1985, LANCET, P695

[5] SCELETIUM ALKALOIDS .12. AZA-RING EXPANSION OF CIS-BICYCLO[4.2.0]OCTANONES AND RELATED-COMPOUNDS - A REGIOSPECIFIC SYNTHESIS OF CIS-OCTAHYDROINDOLONES [J].

JEFFS, PW ;

MOLINA, G ;

CORTESE, NA ;

HAUCK, PR ;

WOLFRAM, J .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3876-3881

[6] CYCLOADDITIONS .24. IMPROVED PROCEDURE FOR ADDITION OF DICHLOROKETENE TO UNREACTIVE OLEFINS [J].

KREPSKI, LR ;

HASSNER, A .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2879-2882

[7] ORGANOALUMINUM-PROMOTED BECKMANN REARRANGEMENT OF OXIME SULFONATES [J].

MARUOKA, K ;

MIYAZAKI, T ;

ANDO, M ;

MATSUMURA, Y ;

SAKANE, S ;

HATTORI, K ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2831-2843

[8] NEW TOTAL SYNTHESIS OF D,L-PUMILIOTOXIN-C VIA AN INDANONE [J].

OPPOLZER, W ;

FEHR, C ;

WARNEKE, J .

HELVETICA CHIMICA ACTA, 1977, 60 (01) :48-58

[9] DIISOBUTYLALUMINUM HYDRIDE - A NOVEL REAGENT FOR THE REDUCTION OF OXIMES [J].

SASATANI, S ;

MIYAZAKI, T ;

MARUOKA, K ;

YAMAMOTO, H .

TETRAHEDRON LETTERS, 1983, 24 (43) :4711-4712

[10]

YU QS, 1988, HETEROCYCLES, V27, P745