[AlphaScent]

Any chance of getting away with the hydroboration reaction below?  Other thoughts? 

How labile is that tertiary alcohol?  Should I protect it before making the a,b unsaturated ester?]

Cheers!

[pgk]

Absolutely, yes. Otherwise you create an endocyclic conjugated system of double bonds. But the protection is difficult due to steric and conformer hindrance.

[AlphaScent]

I agree.  Good call.

[TheUnassuming]

I don't think the hydroboration reaction will go.  Is that reaction known with that sort of system?

[orgopete]

I don't think the hydroboration reaction will go.

I agree. Hydroboration gives an anti-Markovnikov product. I'd argue that with all of the functionality actual conditions may be quite specific. I am tempted to think this can be done in a single step if the oxygen can be made to walk to the tertiary carbon in an electrocyclic or other reaction. For all I know, treating with a mineral acid can do this rearrangement.