[AlphaScent]

Do you think this is reasonable.  I do not know which would be more reactive towards the enolate.  I am just wondering if I can make the bromide (or iodide) early with out having to mono-protect the diol.  Is the thioester more reactive than a bromide? Iodide?

Comparing the Pkas the answer would be I would not get the product I want.

Thanks for the thoughts

[Babcock_Hall]

I am nobody's idea of the next RB Woodward.  However, omega-bromoacids are available in many carbon chain lengths (I don't know how they are made).  Therefore, the first few steps don't seem to be necessary.  Also, I have a question.  Are you proposing to work with an unactivated acid, as opposed to a acyl chloride, for example?

[orgopete]

I'm with Babcock Hall. This has many problems. Kiss your bromine goodbye.