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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X


MARTINEZ-MORA, Eder I. et al. Divergent and Selective Functionalization of 2-Formylpyrrole and its Application in the Total Synthesis of the Aglycone Alkaloid Pyrrolemarumine. J. Mex. Chem. Soc [online]. 2016, vol.60, n.1, pp.23-33. ISSN 1870-249X.

Diverse 1,2- and 1,2,5-substituted pyrroles were efficiently prepared through a regioselective functionalization of 2-formylpyrrole (5a). This methodology was applied for the first total synthesis of pyrrolemarumine (4b), the aglycone of the corresponding natural pyrrole alkaloid 4"-O-α-L-rhamnopyranoside. The synthesis of 4b was achieved starting from 5a through a seven-step process in 28% overall yield.

Keywords : 2-formylpyrrole; Vilsmeier-Haack formylation; pyrrole alkaloids; pyrrolemarumine.

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