Enantioselective Total Synthesis of (+)-Salimabromide Reveals Almost Racemic Nature of Natural Salimabromide

The enantioselective total synthesis of (+)-salimabromide was accomplished by a concise two-step conversion of the fully functionalized dibromo-tetraline core, involving a one-pot Baeyer–Villiger/allylic oxidation by an innovative radical reagent combination. This route unequivocally resolves the st...

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Bibliographic Details
Published in:Organic letters 2019-03, Vol.21 (6), p.1939-1942
Main Authors: Palm, André, Knopf, Christopher, Schmalzbauer, Björn, Menche, Dirk
Format: Article
Language:English
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Summary:The enantioselective total synthesis of (+)-salimabromide was accomplished by a concise two-step conversion of the fully functionalized dibromo-tetraline core, involving a one-pot Baeyer–Villiger/allylic oxidation by an innovative radical reagent combination. This route unequivocally resolves the stereochemistry and reveals the highly unusual, almost racemic nature of natural salimabromide.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00706