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Mechanism Help 1

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youconfusedmetoo:
@clarkstill, I have since figured out/solve the first issue. But I am currently stuck on the NaIO4 part. It should yield a cyclic ether, but I have no idea how H2O can play a role in this.
The paper is: https://pubs.acs.org/doi/abs/10.1021/jacs.7b10177

clarkstill:
THF/water is just a solvent for the NaIO4 cleavage. If you draw the product of that oxidative cleavage reacton you'll find you have an aldehyde and an unprotected alcohol. Can you see how that alcohol and aldehyde might react to form compound 21 from the paper? Compound 21 is known as a hemi-acetal, so you could have a read about their properties/reactivity.

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