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Synthesis of vinca alkaloids and related compounds. Part 110: A new synthetic method for the preparation of pandoline-type alkaloid-like molecules |
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| Authors: | Flórián Tóth György Kalaus István Greiner Ágnes Gömöry Csaba Szántay |
| Institution: | a Department of Organic Chemistry and Technology, Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Gellért tér 4, H-1521 Budapest, Hungary b Centre for Computational Chemistry, School of Chemistry, University of Bristol, Bristol BS8 1TS, UK c Chemical Works of Gedeon Richter Ltd, Gyömr?i út 19-21, H-1103 Budapest, Hungary d Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Gellért tér 4, H-1521 Budapest, Hungary e Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Pusztaszeri út 59-67, H-1025 Budapest, Hungary |
| Abstract: | A practicable synthesis of a pandoline-type alkaloid-like molecule is reported through an efficient preparation of carbinolamine ether intermediates (9a and 9b). The key step of the synthesis consists of an intramolecular cycloaddition of the secodine-type intermediate (2), which was formed from the tryptamine derivative (3) and lactol (4). The mechanism of the cycloaddition reaction was investigated by quantum chemical calculations and it was found to follow a step-wise mechanism involving a zwitterionic intermediate (15). By employing this strategy, other members of the family of pandoline alkaloids or alkaloid-like molecules could be synthesized by reacting the tryptamine derivative with appropriately functionalized aldehydes. |
| Keywords: | Ψ-Aspidospermane alkaloids Pandoline 20-Epipandoline 19-Hydroxy-20-epipandoline Pandoline-like molecule Diels-Alder reaction Reaction mechanism |
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