Two new versatile protected precursors of substituted boldine (1) derivatives have been synthesized, isolated, and fully characterized: 9-O-methoxymethylboldine (5) and 2,9-O,O 0 -dimethoxymethylboldine (6). There was no evidence of the presence of 2-O-methoxymethylboldine (7) in the reaction mixture. These compounds are expected to exhibit an ortho-directing capacity for further aromatic substitution, which constitutes an attractive alternative to the electrophilic substitution of unprotected boldine, as the methoxymethyl group can be easily removed under mild conditions.

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Alkaloids U 0600The Synthesis of Methoxymethyl Derivatives of Boldine: Versatile Protected Precursors of Substituted Boldine Derivatives. -(REVECO*, P. G.; ASENCIO, M.; SANGUINETTI, M. E.; THOMET, F. A.; Synth. Commun. 35 (2005) 3, 341-347; Dep. Quim., Univ. Tec. Federico St. Maria, Valparaiso, Chile; Eng.) -H. Toeppel 30-181