Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine
Jäger, C., Nieger, M., Rissanen, K., & Deska, J. (2023). Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine. European Journal of Organic Chemistry, 26(39), Article e202300288. https://doi.org/10.1002/ejoc.202300288
Julkaistu sarjassa
European Journal of Organic ChemistryPäivämäärä
2023Tekijänoikeudet
© 2023 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH
The assembly of enzymatic cascades and multi-step reaction sequences represents an attractive alternative to traditional synthetic-organic approaches. The biocatalytic reaction mediators offer not only mild conditions and permit the use of environmentally benign reagents, but the high compatibility of different enzymes promises more streamlined reaction setups. In this study, a triple-enzymatic strategy was developed that enables the direct conversion of γ,δ-unsaturated esters to N-hydroxy-γ-lactame building blocks. Hereby, a lipase-catalyzed hydroxylaminolysis generates hydroxamic acid intermediates that are subsequently aerobically activated by horseradish peroxidase and glucose oxidase to cyclize in an intramolecular nitroso ene reaction. Utilizing the hydroxylaminolysis/ene-cyclization sequence for the preparation of an aza-spirocyclic lactam, the multi-enzymatic methodology was successfully employed in the synthesis of key intermediates en route to alkaloids of the Cephalotaxus family.
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Julkaisija
Wiley-VCH VerlagISSN Hae Julkaisufoorumista
1434-193XAsiasanat
Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/184138308
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Lisätietoja rahoituksesta
This work was financial support by the European Research Council (ABIONYS, 865885) and the Ruth & Nils-Erik Stenbäcks Stiftelse. CJ thanks the Finnish Foundation for Technology Promotion and the Orion Research Foundation sr for personal grants.Lisenssi
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