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- Title
Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine.
- Authors
Jäger, Christina; Nieger, Martin; Rissanen, Kari; Deska, Jan
- 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‐lactam 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.
- Subjects
ESTERS; ENE reactions; GLUCOSE oxidase; HYDROXAMIC acids; HORSERADISH peroxidase; HYDROXYLAMINE
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 39, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300288