Please see the other question for instructions. I am also reposting the instructions here. This is in regards to the retro syn you did for me.

 

I need the following done:

 

1. For Compound A: I need an alternative synthesis to this. The suggestion made was to possibly start out with an ester (vice aldehyde) and use LDA (vice NaOEt) as the base. Also, the methylation step apparently needs a chiral auxiliary, so please suggest one and show how it would work. Also, starting with the step involving MCPBA and going through the Grignard, the stereochemistry is being called into question. Is there something else that can be used to ensure that stereochemistry or ? Lastly, protect the amine of the acyl chloride using a Boc group (I also need to know how to deprotect this).

 

2. For Compound B: Protect the alcohol of the starting material with TBDMS-Cl/Et3N. Also, start out with a mono acyl chloride, with an OEt group on the other end. After the first step is done, then show how to make the ester into a Cl group. For the syn dihydroxylation a chiral auxiliary is required, so please suggest one and show how it would work. For the last step, suggest an alternative base to n-BuLi.

 

3. Please update all the ChemDraws accordingly.