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Stereoselective total synthesis of (±)-7-deoxy-trans-dihydronarciclasine, a potent antineoplastic phenanthridone alkaloid |
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| Authors: | Gábor Szántó Lenke Mattyasovszky Ákos Simon |
| Institution: | a Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budafoki út 8, H-1111 Budapest, Hungary b Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budafoki út 8, H-1111 Budapest, Hungary c Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szt. Gellért tér 4, H-1111 Budapest, Hungary |
| Abstract: | A short and efficient stereoselective total synthesis of (±)-7-deoxy-trans-dihydronarciclasine, a highly potent antineoplastic agent and constituent of the Amaryllidaceae alkaloids, is described. Starting from a known arylcyclohexylamine-type precursor 6, the C-ring with the required stereochemistry is constructed using a chemo- and stereoselective enone reduction (NaBH4/CaCl2 system) and a Mitsunobu reaction. For the B-ring closure, the Banwell modification of the Bischler-Napieralski reaction was applied. |
| Keywords: | Alkaloids (± )-7-Deoxy-trans-dihydronarciclasine Stereoselective synthesis |
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