My guess as to the product would be as follows:
- formation of a cyclic iodium(?) ion at the alkene
-5-exo-tet cyclization with the hydroxyl as the nucleophile breaking open the" iodium" ring
-deprotonation to neutralize the newly cyclized oxygen
- displacement of the iodine by the resulting hydroxide, this leads to both oxygens being on the same side of the c-c where the alkene once was.


No idea if this logic holds up, or if im even on the right track... just looking for some suggestions/ideas.

Thanks!

Mphahlele, M.J. "Molecular Iodine-Mediated Cyclization of Tethered Heteroatom-Containing Alkenyl or Alkynyl Systems" Molecules 2009, 14:4814-4837.

Open access review.

Thanks!