Biocatalytic Organic Synthesis of Optically Pure (S)-Scoulerine and Berbine and Benzylisoquinoline Alkaloids
| Autor: | Wolf-Dieter Lienhart, Silvia Wallner, Verena Resch, Wolfgang Kroutil, Johann H. Sattler, Peter Macheroux, Joerg H. Schrittwieser, Jasmin Resch |
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| Rok vydání: | 2011 |
| Předmět: |
Stereochemistry
Berberine Alkaloids 010402 general chemistry Benzylisoquinolines 01 natural sciences Chemical synthesis Article chemistry.chemical_compound Alkaloids Scoulerine Organic chemistry Bischler–Napieralski reaction Enantiomeric excess Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Enantioselective synthesis Total synthesis Stereoisomerism Organic Chemistry Phenomena 0104 chemical sciences Cyclization Biocatalysis Organic synthesis Oxidation-Reduction |
| Zdroj: | The Journal of Organic Chemistry |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo201056f |
| Popis: | A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C-C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 4-8 linear steps using either a Bischler-Napieralski cyclization or a C1-Cα alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 5-9 linear steps. |
| Databáze: | OpenAIRE |
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