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Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes.

ABSTRACT: 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.

SUBMITTER: See YY

PROVIDER: S-EPMC5287264 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes.

See Yi Yang YY Herrmann Aaron T AT Aihara Yoshinori Y Baran Phil S PS

Journal of the American Chemical Society 20151021 43

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 paren ...[more]

PMID: 26466196

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