Tetrahedron p. 209 - 218 (1981)
Update date:2022-08-02
Topics: Oxidation Regioselectivity Column chromatography Yield Stereochemistry Recrystallization Mass spectrometry (MS) Cyclization Precursor TLC (thin-layer chromatography) Alkaloid Retrosynthetic analysis Workup Catalysis Reaction Monitoring Biomimetic Synthesis Solvent extraction NMR spectroscopy (Nuclear Magnetic Resonance)
Adams, Joyce H.
Brown, P. Margaret
Gupta, Padma
Khan, M. Shafig
Lewis, John R.
A biomimetic synthesis of the anti-tumor active alkaloid acronycine (7; R=R'=Me) has been obtained by cyclisation of 6-(2-methylaminobenzoyl)-5,7-dimethoxy-2,2-dimethylchromene (11; R=R'=Me); isoacronycine (20; R=R'=Me) was also produced.In an analogous manner the aminochromene (11; R=H, R'=Me) gave a mixture of des-N-methylacronycine (7; R=H, R'=Me) and des-N-methylisoacronycine (20; R=H, R'=Me).The aminochromenes were best synthesised by condensation of lithio-5,7-dimethoxy-2,2-dimethylchromene (22; R=Li) with N-methylisatoic anhydride (26) or with 2-methyl-3,1-benzoxazin-4-one (21).The relevance of this synthetic route to the biogenesis of acridone alkaloids is discussed.
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Doi:10.1246/bcsj.54.1448
(1981)Doi:10.1016/j.bmcl.2004.08.014
(2004)Doi:10.1021/ja0462777
(2004)Doi:10.1016/j.tetlet.2004.08.166
(2004)Doi:10.1016/S0022-328X(00)85768-X
(1981)Doi:10.1016/S0040-4020(01)92104-0
(1981)
