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Synthesis of vinca alkaloids and related compounds. Part 108: Efficient convergent synthetic pathway to the ibophyllidine skeleton IV. First synthesis of (±)-18-hydroxy-20-epiibophyllidine |
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| Authors: | Flórián Tóth Vajk Dániel Horváth Mária Kajtár-Peredy László Hazai |
| Institution: | a Department for 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-1111 Budapest, Hungary b Chemical Works of Gedeon Richter Ltd, Gyömr?i út 19-21, H-1103 Budapest, Hungary c Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Pusztaszeri út 59-67, H-1025 Budapest, Hungary |
| Abstract: | The first total synthesis of the pentacyclic alkaloid (±)-18-hydroxy-20-epiibophyllidine was realized via an efficient preparation of the d-seco-pseudoaspidospermane molecule. The key step of the sequence involves an intramolecular 4+2] cycloaddition reaction of the dihydrosecodine intermediate, which was built up from the reaction of a tryptamine derivative with an aldehyde-ester. After full epimerization, the intramolecular N-alkylation of the tetracyclic ester gave the pentacyclic compound. Reduction of the latter molecule led to the title compound. |
| Keywords: | 18-Hydroxy-20-epiibophyllidine Ibophyllidine Deethylibophyllidine Indole alkaloids Natural products |
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