tert-Butyl hydroperoxide → (3S,8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-7-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate

Beteiligte Stoffe

Reaktionsschritte

A second method of preparing βAET has been developed which also used 3β,17βdiacetoxyandrost-5-ene as a starting material as before. This compound was oxidized with t-butylhydroperoxide in the presence of chromium hexacarbonyl (Cr(CO)6) to form 3β,17β-diacetoxyandrost-5-en-7-one as described by Pearson [Pearson, et al., J. Chem Soc. Perkin Trans, I, 267 (1985)]. The enone formed then was reduced with triisobutylaluminum (TIBA) to give the acetylated 7β-hydroxy (I) product.

Herkunft & Nachweise