Divergent and Selective Functionalization of 2-Formylpyrrole and its Application in the Total Synthesis of the Aglycone Alkaloid Pyrrolemarumine
DOI:
https://doi.org/10.29356/jmcs.v60i1.67Keywords:
2-formylpyrrole, Vilsmeier-Haack formylation, pyrrole alkaloids, pyrrolemarumineAbstract
Diverse 1,2- and 1,2,5-substituted pyrroles were efficiently prepared through a regioselective functionalization of 2-formylpyr-role (5a). This methodology was applied for the first total synthesis of pyrrolemarumine (4b), the aglycone of the corresponding natural pyr-role alkaloid 4”-O-a-L-rhamnopyranoside. The synthesis of 4b was achieved starting from 5a through a seven-step process in 28% over-all yield.Downloads
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