Chemical transformation of protoberberines. Part 9. A biomimetic synthesis of oxychelerythrine, dihydrochelerythrine, and chelerythrine from berberine
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 2253-2256
- https://doi.org/10.1039/p19860002253
Abstract
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.This publication has 4 references indexed in Scilit:
- Biosynthesis of Benzo[c]phenanthridine Alkaloids Sanguinarine, Chelirubine and MacarpineHelvetica Chimica Acta, 1983
- 8-hydroxydihydrochelerythrine and arnottianamide from roots of Toddalia asiaticaPhytochemistry, 1982
- Chemistry of Benzo [c] phenanthridine Alkaloids having Antineoplastic ActivityYAKUGAKU ZASSHI, 1981
- Studies of enzyme-mediated reactions. Part 9. Stereochemistry of oxidative ring cleavage adjacent to nitrogen during the biosynthesis of chelidonineJournal of the Chemical Society, Perkin Transactions 1, 1979