What is this functional group, and how do you make it

by CrimpJiggler
Tags: functional
CrimpJiggler is offline
Jan21-14, 04:25 AM
P: 149
On an exam question recently, I had to perform a retrosynthesis on a molecule and it had this functional group on it:

it took me by surprise. I decided to cleave the whole thing off, and replace it with a double bond (cuz I know you can make cis diols from double bonds) then things seemed to fall into place cuz the double bond let me do a retro diels alder and finish the question, but I couldn't explain how to make that double oxygen thing. I said you could make it with an osmium tetroxide catalysed reaction, but that doesn't explain the t-butyl group. After the exam, my classmates said it was an acetal protected carbonyl group but how can it be an acetal if the oxygens are attached at different carbons?
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