Enantioselective Synthesis of Oasomycin A, Part III: Fragment Assembly and Confirmation of Structure

Putting the pieces together: The total synthesis of the natural macrolide oasomycin A has been realized. Key fragment couplings include an anti‐Felkin selective aldol addition (green), Kociensky–Julia olefinations (red), and competitive Weinreb amide acylation reaction (blue). The utility of the 4,5...

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Veröffentlicht in:Angewandte Chemie International Edition 2007-01, Vol.46 (4), p.545-548
Hauptverfasser: Evans, David A., Nagorny, Pavel, McRae, Kenneth J., Sonntag, Louis-Sebastian, Reynolds, Dominic J., Vounatsos, Filisaty
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Sprache:eng
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Zusammenfassung:Putting the pieces together: The total synthesis of the natural macrolide oasomycin A has been realized. Key fragment couplings include an anti‐Felkin selective aldol addition (green), Kociensky–Julia olefinations (red), and competitive Weinreb amide acylation reaction (blue). The utility of the 4,5‐diphenyloxazole as a carboxy surrogate and the late‐stage macrolactonization affording the 42‐membered macrocycle of oasomycin A are also described.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200603652