The Acid-catalyzed dienone-phenol rearrangement of androsta-1,4-dien-3,17-dione: the chemical synthesis of 1,17 alpha-dimethyl-1,3,5(10)-estratriene-3,17-beta-diol.

MARÍA L. BOHN; VALERIA JUSTRIBÓ; SEBASTIÁN TESTERO; MARÍA I. COLOMBO; SILVINA C. PELLEGRINET; EDMUNDO A. RÚVEDA

Journal of Undergraduate Chemistry Research

Chemistry Department, Virginia Military Institute

Lugar: Lexington, USA; Año: 2002 vol. 1 p. 33 - 38

1541-6003

The chemical synthesis of 1,17alpha-dimethyl-1,3,5(10)estratriene-3,17beta-diol has been performed in five steps from testosterone propionate. Key steps include the acid catalyzed dienone-phenol-rearrangement of androsta-1,4-dien-3,17dione and a final stereoselective addition of an organocerium compound to 1-methyl estrone.