Steroids are ubiquitous natural products that are found in great abundance and diversity in Nature. Despite the wealth of knowledge gained in the biology and chemistry of steroids through the intense research interests over the past decades, there remain numerous challenges in the field. These include the synthesis of steroids with modified skeletons and the preparation of steroidal compounds that are highly oxidized; and consequently, the biology of these substances are currently under-explored. While many elegant approaches to such targets have been disclosed in the recent years, a general approach to highly oxidized steroids remains elusive.<br/><br/>This poster describes the efforts towards such a goal. Through the sequential and site selective C-H oxidation of a readily available steroid scaffold, the synthesis of advanced oxidized intermediates has been achieved which would serve to pave a way to access steroidal natural product families in a unified fashion. Critical to this effort was the development of an operationally simple, imine directed, copper mediated C-H hydroxylation reaction. Unlike previous precedence, higher yields and broader substrate scope were achieved with significant reduction in reaction time. Some mechanistic details are also discussed.

Scalable copper mediated C-H hydroxylation: Synthesis of polyhydroxylated steroids

253rd National Meeting (2017)

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