Reaction of indole-2,3-dicarboxylic anhydride with (3-bromo-4-pyridyl)triisopropoxytitanium: Synthesis of ellipticine

作者: Yasuyoshi Miki , Yoshitaka Tada , Norihide Yanase , Hiroko Hachiken , Ko-ichi Matsushita

DOI: 10.1016/0040-4039(96)01768-6

关键词: Product (mathematics)Yield (chemistry)EllipticineIndole testChemistryMedicinal chemistry

摘要: Abstract N -Benzylindole-2,3-dicarboxylic anhydride ( 1 ) was reacted with (3-bromo-4-pyridyl)triisopropoxytitanium to give 2-(3-bromoisonicotinoyl)indole-3-carboxylic acid 2 as the sole product in high yield, which could be converted ellipticine six steps.

参考文章(23)
William H. Pearson, Advances in heterocyclic natural product synthesis JAI Press. ,(1990)
D. J. Thompson, K. Smith, Organometallics in synthesis Synthesis. ,vol. 1995, pp. 324- 381 ,(1995) , 10.1039/9781847556134-00324
Deborah A. Davis, Gordon W. Gribble, A regioselective diels-alder synthesis of ellipticine Tetrahedron Letters. ,vol. 31, pp. 1081- 1084 ,(1990) , 10.1016/S0040-4039(00)88731-6
LK Dalton, S Demerac, BC Elmes, JW Loder, JM Swan, T Teitei, Synthesis of the tumour-inhibitory alkaloids, ellipticine, 9-methoxyellipticine, and related pyrido[4,3-b]carbazoles Australian Journal of Chemistry. ,vol. 20, pp. 2715- 2727 ,(1967) , 10.1071/CH9672715
G. W. GRIBBLE, M. G. SAULNIER, Syntheses of ellipticine and related pyridocarbazole alkaloids ― A review Heterocycles. ,vol. 23, pp. 1277- 1315 ,(1985) , 10.1002/CHIN.198539377
Vinod K. Kansal, Pierre Potier, The biogenetic, synthetic and biochemical aspects of ellipticine, an antitumor alkaloid Tetrahedron. ,vol. 42, pp. 2389- 2408 ,(1986) , 10.1016/0040-4020(86)80002-3
Gordon W. Gribble, Mark G. Saulnier, Mukund P. Sibi, Judy A. Obaza-Nutaitis, Synthesis and Diels-Alder reactions of 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole. A new annulation strategy for the construction of ellipticine and isoellipticine Journal of Organic Chemistry. ,vol. 49, pp. 4518- 4523 ,(1984) , 10.1021/JO00197A039
Sandeep P. Modi, Meged A. Michael, Sydney Archer, James J. Carey, An efficient synthesis of C-11 substituted 6H-pyrido[4,3-b]carbazoles Tetrahedron. ,vol. 47, pp. 6539- 6548 ,(1991) , 10.1016/S0040-4020(01)82308-5