Torgov steroid synthesis

The Sarett oxidation I did was a bit longer ago, and on a side project that didn’t go anywhere so I don’t remember it too well. I was trying to do an allylic oxidation to convert a cyclohexene to a cyclohexenone, but the molecule had an acetal and some other sensitive bits and pieces. Surprisingly the Sarett conditions beat the old Corey 2,5-dimethylpyrazine/CrO3 combo, and all the other stuff I tried. I definitely used an excess of Chromium, but probably more like 2-4 equivalents. I don’t remember having problems with the Cr residues, but then it was on small scale again. I don’t know if you can use the same trick that people employ for PDC/PCC in CH2Cl2 where you add something like powdered molecular sieves, silica or alumina to the reaction at the start along with the oxidant to keep things loose. I’ve done that with 20-30 g PCC, and it works great – just add ether/CH2Cl2 and filter off the Cr/absorbant, which then doesn’t stick to the inside of the flask.

Torgov steroid synthesis

torgov steroid synthesis

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torgov steroid synthesis

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