The application of vinylogous iminium salt derivatives to the synthesis of Ningalin B hexamethyl ether |
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| Authors: | John T Gupton Stuart C CloughRobert B Miller John R LukensCharlotte A Henry René PF KantersJames A Sikorski |
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| Institution: | a Department of Chemistry, University of Richmond, Richmond, VA 23173, USA
b AtheroGenics Inc., 8995 Westside Parkway, Alpharetta, GA 30004, USA |
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| Abstract: | A vinylogous iminium salt derivative has been used to prepare a 2,3,4-trisubstituted pyrrole synthon in a regioselective, efficient and convenient manner. This pyrrole synthon was subsequently converted to the multidrug-resistant (MDR) reversal agent, Ningalin B hexamethyl ether, via alkylation, hydrolysis and oxidative lactonization steps. This methodology provides an alternative pathway to this important class of pyrrole containing marine natural products. |
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| Keywords: | chloropropeniminium salt β-chloroenal trisubstituted pyrrole Ningalin B |
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