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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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-11, Vol.137 (43), p.13776-13779
Main Authors: See, Yi Yang, Herrmann, Aaron T, Aihara, Yoshinori, Baran, Phil S
Format: Article
Language:English
Subjects:
Copper - chemistry
Models, Molecular
Molecular Conformation
Oxidation-Reduction
Polymers - chemical synthesis
Polymers - chemistry
Pregnanes - chemical synthesis
Pregnanes - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b09463