Fully aromatised benzo[c]phenanthridine alkaloids, oxychelerythrine (4), dihydrochelerythrine (9), and chelerythrine (10) have been efficiently synthesized from berberine (1), a protoberberine alkaloid, via oxidative C(6)–N bond cleavage, followed by recyclisation between the C-6 and C-13 positions of (1) by a biogenetic process.
M. Hanaoka, T. Motonishi and C. Mukai, J. Chem. Soc., Perkin Trans. 1, 1986, 2253 DOI: 10.1039/P19860002253
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