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Conversion of Natural Narciclasine to Its C-1 and C-6 Derivatives and Their Antitumor Activity Evaluation: Some Unusual Chemistry of Narciclasine |
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| Authors: | Juana Goulart Stollmaier Jared Thomson Mary Ann Endoma-Arias Razvan Simionescu Alexandra Vernaza Nakya Mesa-Diaz Mitchell Smith Liqin Du Alexander Kornienko Tomas Hudlicky |
| Institution: | 1.Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, ON L2S 3A1, Canada; (J.T.); (M.A.E.-A.); (R.S.); (T.H.);2.Department of Chemistry and Biochemistry, Texas State University, San Marcos, TX 78666, USA; (A.V.); (N.M.-D.); (M.S.); (L.D.) |
| Abstract: | During the search for a general, efficient route toward the synthesis of C-1 analogues of narciclasine, natural narciclasine was protected and converted to its C-1 enol derivative using a novel semi-synthetic route. Attempted conversion of this material to its triflate in order to conduct cross-coupling at C-1 resulted in a triflate at C-6 that was successfully coupled with several functionalities. Four novel compounds were fully deprotected after seven steps and subjected to evaluation for cytotoxic activity against three cancer cell lines. Only one derivative showed moderate activity compared to that of narciclasine. Spectral and physical data are provided for all new compounds. |
| Keywords: | narciclasine Amaryllidaceae alkaloids Semi-synthesis natural products |