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 editorsJäger, Christina; Nieger, Martin; Rissanen, Kari; Deska, Jan

Journal or seriesEuropean Journal of Organic Chemistry

ISSN1434-193X

eISSN1099-0690

Publication year2023

Publication date07/08/2023

Volume26

Issue number39

Article numbere202300288

PublisherWiley-VCH Verlag

Publication countryGermany

Publication languageEnglish

DOIhttps://doi.org/10.1002/ejoc.202300288

Publication open accessOpenly available

Publication channel open accessPartially 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.


Keywordsenzymesorganic chemistryorganic compounds


Contributing organizations


Ministry reportingYes

Reporting Year2023

Preliminary JUFO rating1


Last updated on 2024-03-04 at 18:35