Purushottamachar Puranik - A New Simple and High-Yield Synthesis of 5α-Dihydrotestosterone (DHT), a Potent Androgen Receptor Agonist

Version 1

      Publication Details (including relevant citation   information):

      Steroids, 2012, 77(14),  1530-4 PMID: 23044354
      Puranik Purushottamachar and   Vincent C.O. Njar

      Abstract:

      We have devised an efficient procedure for the synthesis of   5α-dihydrotestosterone (DHT) (1) starting from   3β-hydroxy-5α-androstan-17-one, providing the product in   unprecedented 82% yield. A reported method of using toxic Jones   reagent is replaced by milder oxidizing agent (NMO/TPAP) in the   synthesis of a key intermediate   17β-[(tert-butyldimethylsilyl)oxy]-5α-androstan-3-one   (18). This new procedure is   simple, does not require special apparatus/precautions or   chromatographic purification in most of the steps.

      Address (URL): http://www.ncbi.nlm.nih.gov/pubmed/23044354