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.