SYNTHESIS OF EMETINE AND RELATED COMPOUNDS .8. SYNTHESIS OF TUBULOSINE AND ISOTUBULOSINE

被引:19
作者
OPENSHAW, HT
WHITTAKE.N
机构
[1] Wellcome Research Laboratories, Beckenham, Kent
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 01期
关键词
D O I
10.1039/j39690000091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The constitution (Ic) assigned to tubulosine {3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-(1,2,3,4-tetrahydro-6-hydroxy- β-carbolin-1-yl)-2H-benzo[a]quinolizine} has been confirmed by total synthesis from the (-)-ester (II) (ethyl 3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-2-acetate) of known configuration. Isotubulosine (Vc), also produced in the synthesis, has been identified with an alkaloid subsequently isolated from Alangium lamarckii.
引用
收藏
页码:91 / +
页数:1
相关论文
共 9 条
[1]   STRUCTURE SYNTHESIS AND STEREOCHEMISTRY OF DEOXYTUBULOSINE [J].
BATTERSBY, AR ;
MERCHANT, JR ;
RUVEDA, EA ;
SALGAR, SS .
CHEMICAL COMMUNICATIONS, 1965, (14) :315-+
[2]   STRUCTURE OF TUBULOSINE NOVEL ALKALOID FROM POGONOPUS TUBULOSUS (DC.) SCHUMANN [J].
BRAUCHLI, P ;
BUDZIKIEWICZ, H ;
DEULOFEU, V ;
DJERASSI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (09) :1895-&
[3]   CONVENIENT ALTERNATIVE SYNTHESIS OF 5-HYDROXYTRYPTAMINE [J].
BRETHERICK, L ;
WRAGG, WR ;
GAIMSTER, K .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JUL) :2919-&
[4]   ALKALOID STUDIES .54. STRUCTURE OF DEOXYTUBULOSINE AND INTERCONVERSION WITH TUBULOSINE [J].
MONTEIRO, H ;
BUDZIKIE.H ;
DJERASSI, C .
CHEMICAL COMMUNICATIONS, 1965, (14) :317-+
[5]   SYNTHESIS OF EMETINE ANND RELATED COMPOUNDS .5. A STEROCHEMICALLY FAVOURABLE SYNTHESIS OF EMETINE [J].
OPENSHAW, HT ;
WHITTAKER, N .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (MAR) :1461-&
[6]   SYNTHESIS OF TUBULOSINE [J].
OPENSHAW, HT ;
WHITTAKE.N .
CHEMICAL COMMUNICATIONS, 1966, (05) :131-+
[7]   SYNTHESIS OF EMETINE AND RELATED COMPOUNDS .7. UTILITY OF BI-FUNCTIONAL CATALYSTS IN AMINE-ESTER INTERACTIONS [J].
OPENSHAW, HT ;
WHITTAKER, N .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (01) :89-+
[8]  
PAKRASHI SC, 1964, INDIAN J CHEM, V2, P468
[9]  
POPELAK A, 1966, TETRAHEDRON LETT, P5077, DOI 10.1016/S0040-4039(00)90329-0