Pyridone Annulation via Tandem Curtius Rearrangement/6π-Electrocyclization: Total Synthesis of (−)-Lyconadin C

作者: Xiayun Cheng , Stephen P. Waters

DOI: 10.1021/OL401954F

关键词:

摘要: A concise, enantioselective total synthesis of the Lycopodium alkaloid (−)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction a luciduline congener through Mannich-type cyclization one-pot, tandem Curtius rearrangement/6π-electrocyclization to fashion 2-pyridone system lyconadin C.

参考文章(54)
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
John H. MacMillan, Stephen S. Washburne, Interaction of carbonyl compounds with organometallic azides. V. Sorboyl chloride and its conversion to an .alpha.-pyridone Journal of Organic Chemistry. ,vol. 38, pp. 2982- 2984 ,(1973) , 10.1021/JO00957A013
Clayton H. Heathcock, Edward F. Kleinman, Edward S. Binkley, Total synthesis of lycopodium alkaloids: (.+-.)-lycopodine, (.+-.)-lycodine, and (.+-.)-lycodoline Journal of the American Chemical Society. ,vol. 104, pp. 1054- 1068 ,(1982) , 10.1021/JA00368A024
F. Eloy, A. Deryckere, Sur une synthese nouvelle des dérivés de la pyridine Journal of Heterocyclic Chemistry. ,vol. 7, pp. 1191- 1193 ,(1970) , 10.1002/JHET.5570070536
Takayuki Shioiri, Kunihiro Ninomiya, Shunichi Yamada, Diphenylphosphoryl azide. A new convenient reagent for a modified Curtus reaction and for the peptide synthesis. Journal of the American Chemical Society. ,vol. 94, pp. 6203- 6205 ,(1972) , 10.1021/JA00772A052
W. L. Scott, D. A. Evans, Total synthesis of (+-)-luciduline Journal of the American Chemical Society. ,vol. 94, pp. 4779- 4780 ,(1972) , 10.1021/JA00768A083
Drury Caine, Katherine Procter, Roger A. Cassell, A facile synthesis of (-)-R-5-methyl-2-cyclohexen-1-one and related 2-substituted enones from (+)-pulegone Journal of Organic Chemistry. ,vol. 49, pp. 2647- 2648 ,(1984) , 10.1021/JO00188A032
James H. Rigby, Frederick J. Burkhardt, Vinyl isocyanates as aza diene equivalents. A method for the synthesis of functionalized 4-hydroxy-2(1H)-pyridones The Journal of Organic Chemistry. ,vol. 51, pp. 1374- 1376 ,(1986) , 10.1021/JO00358A046
William J. Scott, J. K. Stille, Palladium-catalyzed coupling of vinyl triflates with organostannanes. Synthetic and mechanistic studies Journal of the American Chemical Society. ,vol. 108, pp. 3033- 3040 ,(1986) , 10.1021/JA00271A037
James H. Rigby, N. Balasubramanian, Preparation of highly substituted 2-pyridones by reaction of vinyl isocyanates and enamines Journal of Organic Chemistry. ,vol. 54, pp. 224- 228 ,(1989) , 10.1021/JO00262A047