Efficient Synthesis of a 5α-Reductase Inhibitor

Efficient Synthesis of a 5α-Reductase Inhibitor, 3-(Tetrazol-5-yl)-3,5-pregnadien-20-one through Allylic Rearrangement of Cyanophosphates: H. Yoneyama, Y. Usami and S. Harusawa
Synthesis 2019, DOI: 10.1055/s-0037-1612060


5α-Reductase (5AR) catalyzes the conversion of testosterone into dihydrotestosterone (DHT), which stimulates several growth factors that drive cellular proliferation in the human prostate; therefore, its inhibition is considered a valid therapeutic strategy to treat both benign prostatic hyperplasia and cancer. Professor Shinya Harusawa from Osaka University of Pharmaceutical Sciences (Japan) and co-workers reported a new approach to a 5α-reductase inhibitor, 3-(tetrazol-5-yl)-3,5-pregnadien-20-one, through allylic rearrangement of cyanophosphates (CPs) which have been widely used as synthetic intermediates in organic synthesis. The synthesis of the target molecule from progesterone was completed successfully in 92% overall yield in four steps.

Professor Harusawa said: “The present study helps increasing the diversity of available CPs. In addition, application of this method involving CPs to the synthesis of many biologically important substrates is under investigation in our lab.”
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