Scalable C-H Oxidation with Copper: Synthesis of Polyoxypregnanes

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2015 Oct 15

PMID 26466196

Citations 33

Authors

Yi Yang See

Aaron T Herrmann

Yoshinori Aihara

Phil S Baran

Affiliations

Soon will be listed here.

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.

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