N-[6-(2-HYDROXY-3,4-DIMETHOXY PHENYL)NAPHTHO[2,3-D][1,3]DIOXOL-5-YL]-N-METHYLFORMAMIDE

Description

Arnottianamide occurs in Xanthoxylum arnottianum and, in trace amounts, in X. cuspidatum. It crystallizes as colourless prisms from EtOH and gives an ultraviolet spectrum in ethanol with absorption maxima at 236 and 332 nm and shoulders at 280 and 324 nm. The structure has been elucidated from chemical and spectro-scopic data and confirmed by its preparation from chelerythrine chloride by a Baeyer-Villiger type oxidation of the irnmonium group. Treatment with LiA1H4 gives the deoxo derivative as colourless prisms, m.p. 200-2°C, forming a crystalline methyl derivative, m.p. l66.5-168.5°C.

References

Ishii et al., Tetrahedron Lett., 1203 (1976)