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- Title
Regio- and Stereoselective Biocatalytic Monoamination of a Triketone Enables Asymmetric Synthesis of Both Enantiomers of the Pyrrolizidine Alkaloid Xenovenine Employing Transaminases.
- Authors
Payer, Stefan E.; Schrittwieser, Joerg H.; Grischek, Barbara; Simon, Robert C.; Kroutil, Wolfgang
- Abstract
The (+)- as well as the (−)-enantiomer of the pyrrolizidine alkaloid xenovenine were prepared within five steps with 17 and 30% overall yields, respectively, in optically pure form, >99% ee as well as >99% de. In the asymmetric key step a transaminase performed a regio- and stereoselective monoamination of a triketone. By employing two enantiocomplementary transaminases from Arthrobacter sp. both enantiomers were accessible. The triketone was readily prepared via two steps starting from commercially available, achiral 2-( n-heptyl)furan. In the final catalytic hydrogenation step, the newly introduced chiral centre directed hydrogen addition to form preferentially the desired (5 Z,8 E)-diastereomer. The regio- and stereoselective amination of a single ketone moiety out of three allowed the performance of the shortest and highest yielding total synthesis of the bicyclic showcase pyrrolizidine alkaloid without the need for protecting strategies.
- Subjects
ENANTIOMERS; OPTICAL isomers; CHIRAL stationary phases; PYRROLIZIDINES; ALKALOIDS
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 3, p444
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201500781