I want to replicate the third step, but there seems to be no reaction in an alkaline environment. However, sodium hydroxide is used in the literature. Should I switch to an acidic environment
Depending on what the protecting group and the R's are, that looks awfully sterically hindered. My guess is that the base is removing the proton, but the action of the carbanion is not getting to the aldehyde carbon.
I assume you have water around since you are trying sodium hydroxide, water in the solvent is going to hydrogen bond to all those oxygen, making the steric situation even worse.
I suspect acid catalysis might be similar. It would protonate all those oxygens and all the surrounding positive charge would not help the situation. It might help to get out of hydrogen-bonding solvent with a non-aqueous base, but getting around steric problems could still be difficult. Since I don't know your protecting groups, I cannot speak to that, but I would keep them as small as possible too.
Having the ortho oxygens cannot help as they will repulse the anion with their lone electrons.
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