A biocatalytic hydroxylation-enabled unified approach to C19-hydroxylated steroids

Junlin Wang, Yanan Zhang, Huanhuan Liu, Yong Shang, Linjun Zhou, Penglin Wei, Wen-Bing Yin, Zixin Deng, Xudong Qu () and Qianghui Zhou ()
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Junlin Wang: Wuhan University
Yanan Zhang: Wuhan University
Huanhuan Liu: Wuhan University
Yong Shang: Wuhan University
Linjun Zhou: Wuhan University
Penglin Wei: Chinese Academy of Sciences
Wen-Bing Yin: Chinese Academy of Sciences
Zixin Deng: Wuhan University
Xudong Qu: Wuhan University
Qianghui Zhou: Wuhan University

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C19-OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis.

Date: 2019
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DOI: 10.1038/s41467-019-11344-0

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