A1 Journal article (refereed)
Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine (2023)
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
JYU authors or editors
Publication details
All authors or editors: Jäger, Christina; Nieger, Martin; Rissanen, Kari; Deska, Jan
Journal or series: European Journal of Organic Chemistry
ISSN: 1434-193X
eISSN: 1099-0690
Publication year: 2023
Publication date: 07/08/2023
Volume: 26
Issue number: 39
Article number: e202300288
Publisher: Wiley-VCH Verlag
Publication country: Germany
Publication language: English
DOI: https://doi.org/10.1002/ejoc.202300288
Publication open access: Openly available
Publication channel open access: Partially open access channel
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/88928
Abstract
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.
Keywords: enzymes; organic chemistry; organic compounds
Contributing organizations
Ministry reporting: Yes
Reporting Year: 2023
JUFO rating: 1
