Synthesis and Absolute Configuration of (−)-Normalindine
作者： Masashi Ohba , Hiroyuki Kubo , Tozo Fujii , Hiroyuki Ishibashi , Melvyn V. Sargent
DOI: 10.1016/S0040-4039(97)01568-2
关键词: Enantioselective synthesis 、 Ophiorrhiza 、 Intramolecular force 、 Chemistry 、 Stereochemistry 、 Strychnos 、 Normalindine 、 Absolute configuration
摘要: The first chiral synthesis of the Strychnos and Ophiorrhiza alkaloid (−)-normalindine has been accomplished through a route starting from l-alanine methyl ester exploiting intramolecular oxazole-olefin Diels-Alder reaction. As result, absolute stereochemistry normalindine defined as represented by formula (−)-1. © 1997 Elsevier Science Ltd.
elsevier.com
sci-hub.se 参考文章(21)
K. Ninomiya, T. Shioiri, S. Yamada, Phosphorus in organic synthesis—VII Tetrahedron. ,vol. 30, pp. 2151- 2157 ,(1974) , 10.1016/S0040-4020(01)97352-1
T. Shioiri, Y. Yokoyama, Y. Kasai, S. Yamada, Phosphorus in organic synthesis—XI Amino acids and peptides—XXI : Reaction of diethyl phosphorocyanidate(DEPC) with carboxylic acids. A new synthesis of carboxylic esters and amides Tetrahedron. ,vol. 32, pp. 2211- 2217 ,(1976) , 10.1016/0040-4020(76)85134-4
Joseph Vercauteren, Catherine Lavaud, Jean Levy, Georges Massiot, Activated alkynes as partners in Pictet-Spengler condensations Journal of Organic Chemistry. ,vol. 49, pp. 2278- 2279 ,(1984) , 10.1021/JO00186A037
Georges Massiot, Philippe Thépenier, Marie-José Jacquier, Louisette Le Men-Olivier, Robert Verpoorte, Clément Delaude, Alkaloids of Strychnos johnsonii Phytochemistry. ,vol. 26, pp. 2839- 2846 ,(1987) , 10.1016/S0031-9422(00)83601-8
Herbert Waldmann, Gunther Schmidt, Martin Jansen, Jutta Geb, ASYMMETRIC STEERING OF THE PICTET-SPENGLER REACTION BY MEANS OF AMINO-ACID ESTERS AS CHIRAL AUXILIARY GROUPS Tetrahedron. ,vol. 50, pp. 11865- 11884 ,(1994) , 10.1016/S0040-4020(01)89301-7
Satyesh C. Pakrashi, Bhim C. Maiti, Venkatachalam S. Giri, Synthesis of the alkaloids (±)-normalindine and (±)-norisomalindine Heterocycles. ,vol. 31, pp. 847- 850 ,(1990) , 10.3987/COM-89-5306
Richard P. Polniaszek, Julia A. McKee, Stereoselective reductions of chiral iminium ions Tetrahedron Letters. ,vol. 28, pp. 4511- 4514 ,(1987) , 10.1016/S0040-4039(00)96550-X
Michael P. Doyle, Joseph F. Dellaria, Bernard Siegfried, Stephen W. Bishop, Reductive deamination of arylamines by alkyl nitrites in N,N-dimethylformamide. A direct conversion of arylamines to aromatic hydrocarbons Journal of Organic Chemistry. ,vol. 42, pp. 3494- 3498 ,(1977) , 10.1021/JO00442A009
Ferdinand Bohlmann, Lupinen-Alkaloide, VIII. Zur Konfigurationsbestimmung von Chinolizidin-Derivaten Chemische Berichte. ,vol. 91, pp. 2157- 2167 ,(1958) , 10.1002/CBER.19580911023
Rolf Schröder, Ulrich Schöllkopf, Ernst Blume, Inga Hoppe, Synthesen mit α-metallierten Isocyaniden, XXVIII1) In 2-Stellung unsubstituierte Oxazole aus α-metallierten Isocyaniden und Acylierungsreagenzien Justus Liebigs Annalen der Chemie. ,vol. 1975, pp. 533- 546 ,(1975) , 10.1002/JLAC.197519750315