Total Synthesis of (−)-Colchicine by an Oxyallyl [4+3] Cycloaddition

作者: Jae Chol Lee , Jin Kun Cha

DOI: 10.1016/S0040-4020(00)00862-0

关键词: ChemistryCycloadditionIntramolecular forceTotal synthesisOrganic chemistryEnantioselective synthesisTandemIsocolchicineBiochemistryDrug discovery

摘要: … The desired cycloadduct 7 (R 1 =O-t-Bu) was indeed obtained as a single diastereomer in 45% yield (based on 50% conversion of the starting material). Regiochemistry was firmly …

参考文章(19)
Takahiro Nakamura, Yasuhiro Murase, Ryozo Hayashi, Yonekichi Endo, Studies on the Total Synthesis of dl-Colchiceine. I. Synthesis of 3-Hydroxy-9, 10, 11-trimethoxy-1, 2, 3, 4, 6, 7-hexahydro-5H-dibenzo [a, c] cycloheptatrien-5-one. Chemical & Pharmaceutical Bulletin. ,vol. 10, pp. 281- 290 ,(1962) , 10.1248/CPB.10.281
Baldur Föhlisch, Stefan Sendelbach, Harald Bauer, Spaltung der Sauerstoffbrücke in 8-Oxabicyclo [3.2.1] octan-3-onen und -oct-6-en-3-onen durch Trimethylsilyltrifluormethansulfonat European Journal of Organic Chemistry. ,vol. 1987, pp. 1- 5 ,(1987) , 10.1002/JLAC.198719870102
A.M. van Leusen, B.E. Hoogenboom, H. Siderius, A novel and efficient synthesis of oxazoles from tosylmethylisocyanide and carbonyl compounds Tetrahedron Letters. ,vol. 13, pp. 2369- 2372 ,(1972) , 10.1016/S0040-4039(01)85305-3
Andrew S. Kende, Pawel Fludzinski, Chloroacetylenes as Michael acceptors. I. mechanism of enolate dichlorovinylation. Tetrahedron Letters. ,vol. 23, pp. 2369- 2372 ,(1982) , 10.1016/S0040-4039(00)87344-X
Daniel L. Flynn, Robert E. Zelle, Paul A. Grieco, A mild two-step method for the hydrolysis of lactams and secondary amides Journal of Organic Chemistry. ,vol. 14, pp. 2424- 2426 ,(1983) , 10.1021/JO00162A028
H. M. R. Hoffmann, K. E. Clemens, R. H. Smithers, Stereospecific generation of 2-oxyallylic cations from two new sources. Steric course of cycloaddition to conjugated dienes Journal of the American Chemical Society. ,vol. 94, pp. 3940- 3946 ,(1972) , 10.1021/JA00766A047
Jae Du Ha, Jin Kun Cha, Total Synthesis of Clavepictines A and B. Diastereoselective Cyclization of δ-Aminoallenes Journal of the American Chemical Society. ,vol. 121, pp. 10012- 10020 ,(1999) , 10.1021/JA9925958
E. J. Corey, Raman K. Bakshi, Saizo Shibata, Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications Journal of the American Chemical Society. ,vol. 109, pp. 5551- 5553 ,(1987) , 10.1021/JA00252A056
J. Schreiber, W. Leimgruber, M. Pesaro, P. Schudel, T. Threlfall, A. Eschenmoser, Synthese des Colchicins Helvetica Chimica Acta. ,vol. 44, pp. 540- 597 ,(1961) , 10.1002/HLCA.19610440225
Shinichi Itsuno, Koichi Ito, Akira Hirao, Seiichi Nakahama, Asymmetric reduction of aromatic ketones with the reagent prepared from (S)-(–)-2-amino-3-methyl-1,1-diphenylbutan-1-ol and borane Journal of The Chemical Society, Chemical Communications. pp. 469- 470 ,(1983) , 10.1039/C39830000469