| Autor: |
Robert C, Simon, Christine S, Fuchs, Horst, Lechner, Ferdinand, Zepeck, Wolfgang, Kroutil |
| Rok vydání: |
2014 |
| Předmět: |
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| Zdroj: |
European Journal of Organic Chemistry |
| ISSN: |
1434-193X |
| Popis: |
A short and efficient total synthesis of the alkaloid isosolenopsin and its enantiomer has been achieved. The key step was a ω-transaminase-catalysed regioselective monoamination of the diketone pentadecane-2,6-dione, which was obtained in a single step through the application of a Grignard reaction. Initial low conversions in the biotransformation could be overcome by optimisation of the reaction conditions employing suitable cosolvents. In the presence of 20 vol.-% N,N-dimethylformamide (DMF) or n-heptane the best results were obtained by employing two enantiocomplementary ω-transaminases originating from Arthrobacter at 30–40 °C; under these conditions, conversions of more than 99 % and perfect stereocontrol (ee > 99 %) were achieved. Diastereoselective chemical reduction (H2/Pd/C) of the biocatalytic product gave the target compound. The linear three-step synthesis provided the natural product isosolenopsin in diastereomerically pure form (ee > 99 %, dr = 99:1) with an overall yield of 64 %. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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