A simple and practical approach to the synthesis of the marine sponge pigment fascaplysin and related compounds
| Autor: | George B. Elyakov, Oleg S. Radchenko, V. L. Novikov |
|---|---|
| Rok vydání: | 1997 |
| Předmět: |
chemistry.chemical_classification
Tryptamine Ketone biology Organic Chemistry Salt (chemistry) biology.organism_classification Antimicrobial Biochemistry Sponge Pigment chemistry.chemical_compound chemistry visual_art Yield (chemistry) Drug Discovery visual_art.visual_art_medium Organic chemistry Dehydrogenation |
| Zdroj: | Tetrahedron Letters. 38:5339-5342 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/s0040-4039(97)01167-2 |
| Popis: | Fascaplysin 1, an antimicrobial and cytotoxic red pigment of the marine sponge Fascaplys-inopsis sp., has been synthesized in five steps from tryptamine 2 in 44% overall yield. The key steps in the synthesis are: (a) dehydrogenation of the dihydro-β-carboline intermediate 4 simultaneously with its benzylic oxidation on treatment with MnO2 and (b) the thermal cyclization of the resulting β-carboline 7 into a quaternary salt 8. Similarly, indoloisoquinolines 15 and 16, the tetracyclic analogues of 1, were prepared in six steps from α-amino ketone 9 in 59 and 55% overall yields, respectively. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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