59190-67-9Relevant academic research and scientific papers
RUTACEOUS CONSTITUENTS-13 A BIOMIMETIC SYNTHESIS OF ACRONYCINE
Adams, Joyce H.,Brown, P. Margaret,Gupta, Padma,Khan, M. Shafig,Lewis, John R.
, p. 209 - 218 (2007/10/02)
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.
