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N-tosyl-1,2,3-triazoles as scaffolds for morpholines: the total synthesis of (–)-chelonin A
journal contribution
posted on 2023-05-21, 16:16 authored by Nina GunawanNina Gunawan, Nutt, MJ, Alexander BissemberAlexander Bissember, Jason SmithJason Smith, Stewart, SGSubstituted morpholine derivatives appear frequently in biologically active compounds and thus novel routes towards such structures are of great synthetic interest. Herein, we report the total syntheses of chelonin A, a morpholine-derived marine natural product with reported antibacterial and anti-inflammatory activity. The key step in this process was a rhodium carbenoid 1,3-insertion into a bromohydrin O–H bond, followed by annulation, leading to a 2,6-disubstituted-3,4-dihydro-2H-1,4-oxazine core. This work was then extended to deliver the first asymmetric total synthesis of (–)-chelonin A using an enantioenriched bromohydrin, prepared in turn via asymmetric transfer hydrogenation of an α-bromoketone.
Funding
Australian Research Council
History
Publication title
SynlettVolume
34Pagination
1-5ISSN
0936-5214Department/School
School of Natural SciencesPublisher
Georg Thieme Verlag KgPlace of publication
Rudigerstr 14, Stuttgart, Germany, D-70469Rights statement
© 2022. Thieme. All rights reserved.Repository Status
- Restricted