A preliminary kinetic study of the methylation of boldine with diazome
thane to afford glaucine, based on H-1-NMR spectra recorded at differe
nt times, showed that this reaction proceeds via both N-methyllaurotet
anine (2-O-methylboldine) and predicentrine (9-O-methylboldine). Methy
lation at the 9-O-position is faster and consequently, at stages in wh
ich most of the precursor has been consumed, only predicentrine and gl
aucine accumulate in isolable amounts.