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. Author manuscript; available in PMC: 2011 Mar 10.
Published in final edited form as: J Am Chem Soc. 2010 Mar 10;132(9):2983–2990. doi: 10.1021/ja908395r

Scheme 4.

Scheme 4

Proposed fragmentation of the experimentally documented pentacyclic intermediate (shown in the tautomeric forms 2a and 2b). The different fragmentation paths originating from the two tautomeric forms afford either 4 and 5 or 1 and 8 (i.e. the neutral and exomethylene anion form of the 6,7-dimethyl-8-ribityllumazine).