Total synthesis of (±)-cocculolidine

作者: Tsuneomi Kawasaki , Naoko Onoda , Hidenori Watanabe , Takeshi Kitahara

DOI: 10.1016/S0040-4039(01)01650-1

关键词:

摘要: Abstract A non-aromatic erythrina alkaloid, cocculolidine ( 1 ), which has insecticidal activity, was synthesized efficiently employing coupling reaction of imine with tetronic acid and intramolecular 1,6-addition as the key steps.

参考文章(13)
J. G. Greslin, Klaus Unna, Michael Kniazuk, PHARMACOLOGIC ACTION OF ERYTHRINA ALKALOIDS I. β-ERYTHROIDINE AND SUBSTANCES DERIVED FROM IT Journal of Pharmacology and Experimental Therapeutics. ,vol. 80, pp. 39- 52 ,(1944)
Paul G. Gassman, Stephen J. Burns, General method for the synthesis of enol ethers (vinyl ethers) from acetals Journal of Organic Chemistry. ,vol. 53, pp. 5574- 5575 ,(1988) , 10.1021/JO00258A043
Colin G. Pitt, Zhong-Wei Gu, Peter Ingram, R. Wayne Hendren, The synthesis of biodegradable polymers with functional side chains Journal of Polymer Science Part A: Polymer Chemistry. ,vol. 25, pp. 955- 966 ,(1987) , 10.1002/POLA.1987.080250402
David Megirian, I. H. Slater, D. E. Leary, The action of some derivatives of beta-erythroidine on peripheral neuro-effector systems. Journal of Pharmacology and Experimental Therapeutics. ,vol. 113, pp. 212- 227 ,(1955)
Giovanni Poli, Giuliano Giambastiani, Barbara Pacini, Pd(0)-catalyzed allylic alkylation/Heck coupling in domino sequence ☆ Tetrahedron Letters. ,vol. 42, pp. 5179- 5182 ,(2001) , 10.1016/S0040-4039(01)00951-0
Kojiro Wada, Shingo Marumo, Katsura Munakata, An insecticidal alkaloid, cocculolidine from Tetrahedron Letters. ,vol. 7, pp. 5179- 5184 ,(1966) , 10.1016/S0040-4039(01)89302-3
Kojiro WADA, Shingo MARUMO, Katsura MUNAKATA, An Insecticidal Alkaloid, Cocculolidine from Cocculus trilobus DC Agricultural and biological chemistry. ,vol. 31, pp. 1187- 1189 ,(1967) , 10.1271/BBB1961.32.1187
Heinz Lüllmann, Über das Curare-artige Wirkprinzip der Erythrina-Alkaloide Naunyn-Schmiedebergs Archiv f�r Pharmakologie und Experimentelle Pathologie. ,vol. 258, pp. 91- 107 ,(1967) , 10.1007/BF00535785
Jürgen Maischein, Elmar Vilsmaier, Herstellung und Thermolyse von Hydroxyalken-Lactonen oder Lactamen mit einem Morpholinobicycloalkyl-Rest European Journal of Organic Chemistry. ,vol. 1988, pp. 355- 369 ,(1988) , 10.1002/JLAC.198819880409