N-Tosyl-1,2,3-triazoles as Scaffolds for Morpholines: The Total Synthesis of (–)-Chelonin A
| Autor: | Scott G. Stewart, Jason A. Smith, Alex C. Bissember, Nina Gunawan, Michael J. Nutt |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Synlett. |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/a-1982-5433 |
| Popis: | 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-3,4-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. |
| Databáze: | OpenAIRE |
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