[Morderkerl]

I have this product (attached) and cant seem to reduce the ketone.I have tried NaBH4, the Meerwein-Ponndorf-Verley Reduction, Luche reduction, but none of these seem to do anything. I only extract the reactant. I have also tried these reactoins at different reaction conditions. I also tried LiAlH4, but from NMR studies it seems that there are rearrangement within the molecule (i thing it has to do the the incredible steric hindrance and thus the Hydride attacks the carbons) although the ketone is reduced, but it does not help if i don't have other (and more than one) product/s. Any suggestions?   

[azmanam]

Is this practical or theoretical?  that is, is it homework or are you actually trying this at the bench?

On paper, any of those should work.  In practice, you have one hell of a hindered ketone.  You want your reductant to be AS SMALL as possible.  If NaBH4 didn't work, you might be in trouble.  Maybe you'll get lucky with NaH (and hope it doesn't just enolize the ketone).  You can try selectride, and again maybe you'll get lucky.

You  might also see reduction with H2, Pt or Ni at higher pressures.

[mreff555]

That is a lot of steric hinderance. I would try H2 and Pt, Not ideal lab conditions but that really isn't an ideal reduction. 

Is this practical or theoretical?  that is, is it homework or are you actually trying this at the bench?

On paper, any of those should work.  In practice, you have one hell of a hindered ketone.  You want your reductant to be AS SMALL as possible.  If NaBH4 didn't work, you might be in trouble.  Maybe you'll get lucky with NaH (and hope it doesn't just enolize the ketone).  You can try selectride, and again maybe you'll get lucky.

You  might also see reduction with H2, Pt or Ni at higher pressures.

[Morderkerl]

Thanks for your input, unfortunately it is for my masters project and a key step in my synthesis. But I will try NaH and H2 at high pressure.