Scalable C–H Oxidation with Copper: Synthesis of Polyoxypregnanes
Steroids bearing C12 oxidations are widespread in nature, yet only one preparative chemical method addresses this challenge in a low-yielding and not fully understood fashion: Schönecker’s Cu-mediated oxidation. This work shines new light onto this powerful C–H oxidation method through mechanistic...
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Veröffentlicht in: | Journal of the American Chemical Society 2015-11, Vol.137 (43), p.13776-13779 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Steroids bearing C12 oxidations are widespread in nature, yet only one preparative chemical method addresses this challenge in a low-yielding and not fully understood fashion: Schönecker’s Cu-mediated oxidation. This work shines new light onto this powerful C–H oxidation method through mechanistic investigation, optimization, and wider application. Culminating in a scalable, rapid, high-yielding, and operationally simple protocol, this procedure is applied to the first synthesis of several parent polyoxypregnane natural products, representing a gateway to over 100 family members. |
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ISSN: | 0002-7863 1520-5126 |
DOI: | 10.1021/jacs.5b09463 |