L-Tryptophan, methyl ester → 8-Hydroxyquinoline
반응식
COC(C1C=C2C(=C([C:18]3[CH:19]=[CH:20][C:21]4[C:28](=O)[CH:27]=[C:26](N)[C:24](=[O:25])[C:22]=4[N:23]=3)N=1)NC1C=CC=CC2=1)=O.C(OC1C=CC=C2C=1N=C(C=O)C=C2)C1C=CC=CC=1.COC(=O)[C@H](CC1C2C(=CC=CC=2)NC=1)N>>[OH:25][C:24]1[CH:26]=[CH:27][CH:28]=[C:21]2[C:22]=1[N:23]=[CH:18][CH:19]=[CH:20]2참가 물질
4
실험 절차
Hibino's group has reported the synthesis of demethyllavendamycin methyl ester (C) in Hibino et al., Heterocycles, 20, 1957 (1983). Hibino's group synthesized demethyllavendamycin methyl ester by a Pictet-Spengler type cyclization of 8-benzyloxyquinoline-2-aldehyde with tryptophan methyl ester, followed by aromatization and hydrogenation to give an 8-hydroxyquinoline intermediate. This intermediate was brominated to give the 5,7-dibromo-8-hydroxyquinoline. Oxidation of the 5,7-dibromo-8-hydroxyquinoline yielded the 7-bromoquinolinequinone, and replacement of the bromine with sodium azide, followed by reduction of the azide with sodium hydrosulfite, yielded demethyllavendamycin methyl ester.