[raney nickel]

I was asked to make testosterone from DHEA and this is what I have planned, but I also have a few questions about alternatives.


Q1. I thought about using chlorotrimethylsilane as a blocking group for those hydroxyl groups.  Any arguments against it/for it?

Q2. anything else you see I'm missing?

[sjb]

A few points, as requested.

I'm not overly sure H₂/Ra. Ni is selective enough to reduce the ketone in the presence of the alkene, maybe try NaBH₄ or something.

I'd rather use a silyl protecting group instead of both ester style - I don't think you'd be able to (that) cleanly just deprotect the acetate before your Oppenauer. Look into orthogonal protection strategies.