RUTACEOUS CONSTITUENTS-13 A BIOMIMETIC SYNTHESIS OF ACRONYCINE

DOI: 10.1016/S0040-4020(01)97737-3

Source and publish data:

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)

Authors:

Adams, Joyce H.

Brown, P. Margaret

Gupta, Padma

Khan, M. Shafig

Lewis, John R.

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Article abstract of DOI:10.1016/S0040-4020(01)97737-3

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.