Synthesis of naucléfine, angustidine, angustine, (±)-13b,14-dihydro-angustine and naulafine

作者: David B. Repke , Jahangir , Robin D. Clark , Janis T. Nelson , David B. MacLean

DOI: 10.1016/S0040-4020(01)80085-5

关键词:

摘要: Abstract The lithio derivatives of 3-cyano-4-methylpyridines and 6,7-dihydro-5H-2-pyrindine-4-carbonitrile react with 2,9-bis-(trimethylsilyl)-3,4-dihydropyrido[3,4-b]indolium trifluoromethanesulfonate to form cyclic amidines which, upon hydrolysis oxidation, produce the title alkaloids.

参考文章(30)
Tetsuji. Kametani, Mitsuhiro. Takeshita, Masataka. Ihara, Keiichiro. Fukumoto, Studies on the syntheses of heterocyclic compounds. 657. Total synthesis of angustine, nauclefine, and gentianine Journal of Organic Chemistry. ,vol. 41, pp. 2542- 2545 ,(1976) , 10.1021/JO00877A007
Peter P. Fu, Ronald G. Harvey, Dehydrogenation of polycyclic hydroaromatic compounds Chemical Reviews. ,vol. 78, pp. 317- 361 ,(1978) , 10.1021/CR60314A001
Abbas Shafiee, Ekkehard Winterfeldt, Reaktionen an Indolderivaten, XXI. Die biogenetisch orientierte Totalsynthese von Angustidin und Dihydroangustin Chemische Berichte. ,vol. 107, pp. 966- 974 ,(1974) , 10.1002/CBER.19741070324
Jahangir, David B. MacLean, Herbert L. Holland, Preparation of 8-methylberberines and aza analogues: Synthesis of (±)-alamaridine Canadian Journal of Chemistry. ,vol. 65, pp. 727- 733 ,(1987) , 10.1139/V87-123
S. Grego, D. Tricoli, G. Di Marco, Comparison of homoserine dehydrogenase from different plant sources Phytochemistry. ,vol. 19, pp. 1619- 1623 ,(1980) , 10.1016/S0031-9422(00)83781-4
Françoise Hotellier, Pierre Delaveau, Jean-Louis Pousset, Nauclefine et naucletine deux nouveaux alcaloides de type indoloquinolizidine isoles du Nauclea latifolia Phytochemistry. ,vol. 14, pp. 1407- 1409 ,(1975) , 10.1016/S0031-9422(00)98638-2
Edwin M. Kaiser, Gregory J. Bartling, William R. Thomas, Susan B. Nichols, Diane R. Nash, Selective metalations of methylated pyridines and quinolines. Condensation reactions Journal of Organic Chemistry. ,vol. 38, pp. 71- 75 ,(1973) , 10.1021/JO00941A013
GWK Cavill, A Zeitlins, Corrigenda - Synthesis of D-(+)-tecostidine and related actinidine derivatives Australian Journal of Chemistry. ,vol. 20, pp. 349- 357 ,(1967) , 10.1071/CH9670349C