Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 43, Pages 13776-13779Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b09463
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Funding
- NIH [GM-097444]
- LEO Pharma
- NSS (Ph.D.) A*STAR
- Hewitt Foundation
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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: Schonecker'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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