RAPID SYNTHESES OF SOME INDOLE ALKALOIDS OF THE CALABAR BEAN

被引：35

作者：

HORNE, S ^{[1
]}

TAYLOR, N ^{[1
]}

COLLINS, S ^{[1
]}

RODRIGO, R ^{[1
]}

机构：

[1] UNIV WATERLOO,DEPT CHEM,GUELPH WATERLOO CTR,GRAD WORK CHEM,WATERLOO N2L 3G1,ONTARIO,CANADA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期

关键词：

D O I：

10.1039/p19910003047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rapid, efficient route to 3,3-disubstituted oxindoles from omicron-iodo anilines has been developed. It involves the cyclisation of the corresponding fumarate amides 4 and 15 with butyllithium at -100-degrees-C in the presence of an excess of trimethylchlorosilane. An X-ray crystal structure of 4 suggests that the speed and efficiency of this intramolecular Michael addition is dependent on the conformation adopted by 4 which is particularly suitable for the reaction. This method has been applied to the synthesis of the alkaloids physovenine, physostigmine and esermethole in very high overall yields.

引用

页码：3047 / 3051

页数：5

共 11 条

[1]

BROSSI A, 1989, J ORG CHEM, V54, P1782

[2]

HOFFMANN HMR, 1989, TETRAHEDRON, V45, P6113

[3] CARBON-DIOXIDE - A REAGENT FOR THE SIMULTANEOUS PROTECTION OF NUCLEOPHILIC CENTERS AND THE ACTIVATION OF ALTERNATIVE LOCATIONS TO ELECTROPHILIC ATTACK - .3. A NEW SYNTHETIC METHOD FOR THE ORTHO-SUBSTITUTION OF N-MONOALKYLANILINES [J].

KATRITZKY, AR ;

FAN, WQ ;

AKUTAGAWA, K .

TETRAHEDRON, 1986, 42 (14) :4027-4034

[4]

LEE TBK, 1991, J ORG CHEM, V50, P872

[5]

LUO YL, 1990, HETEROCYCLES, V31, P283

[6]

OKEDA M, 1977, J CHEM SOC P1, P1770

[7] DIASTEREOTOPIC EFFECT OF THE METHYLENE PROTONS IN N-ORTHO-SUBSTITUTED-N-BETA-CYANOETHYLANILIDES - X-RAY STRUCTURE OF N-(BETA-CYANOETHYL)-2'-CHLOROMALEANILIC ACID [J].

RODRIGUEZ, JG ;

CANOIRA, L ;

CALDERON, CE ;

MARTINEZRIPOLL, M ;

BLANCO, SG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (02) :199-203

[8]

ROSENMUND P, 1979, LIEBIGS ANN CHEM, P927

[9] TOTAL SYNTHESES OF (+/-)-PHYSOVENINE AND (+/-)-PHYSOSTIGMINE - AN APPLICATION OF TANDEM ELECTROCYCLIC-[3,3]SIGMATROPIC REACTION OF BENZOCYCLOBUTENES [J].

SHISHIDO, K ;

SHITARA, E ;

KOMATSU, H ;

HIROYA, K ;

FUKUMOTO, K ;

KAMETANI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) :3007-3011

[10]

Takano S., 1989, ALKALOIDS, V36, P225

← 1 2 →