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Paper | Special issue | Vol 73, No. 1, 2007, pp.769-775
Published online, 9th October, 2007
DOI: 10.3987/COM-07-S(U)57
Synthesis of Isodecarine

Jakub Styskala, Petr Cankar, Miroslav Soural, Jan Hlavac,* Pavel Hradil, Jaroslav Vicar, and Vilim Simanek

*Department of Organic Chemistry, Faculty of Science, Palacky University, Tr. Svobody 8, 771 46 Olomouc, Czech Republic

Abstract

The cyclization of 3-bromo-6-methoxy-2-(naphtho[2,3-d][1,3]dioxol-5-ylaminomethyl)phenol (2) using tributyltinhydride under radical-mediated conditions was accompanied by spontaneous oxidation and afforded directly isodecarine (2-methoxy[1,3]benzodioxolo[5,6-c]phenanth-ridin-1-ol, (3). 2-Methoxy-6-(naphtho[2,3-d][1,3]dioxol-5-ylaminomethyl)-phenol (4) was isolated as a side product. Isodecarine was also prepared by the catalytic debenzylation of 7-benzyloxy-8-methoxy-2,3-methylendioxybenzo-[c]phenanthridine (5). This compound was efficiently converted to 7-benzyloxy-8-methoxy-5-methyl-2,3-methylenedioxybenzo[c]phenanthridi-nium trifluoromethanesulfonate (6) in high yield and with a short reaction time.