N-Tosyl-1,2,3-triazoles as Scaffolds for Morpholines: The Total Synthesis of (-)-Chelonin A
SYNLETT(2023)
摘要
Substituted 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-3,4dihydro-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 ?-bromoketone.
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关键词
chelonin A,morpholine,total synthesis,rhodium catalysis,triazole,asymmetric transfer hydrogenation
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