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Are there any synthetic options to add a hydroxyl group at the terminal position to the bicyclo compound below? What might be reactions worth trying, any idea? Or is this a lost cause?

enter image description here

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Or is this a lost cause?

I don't think so. This looks like a good candidate for an allylic oxidation with selenium dioxide, look here for some examples.

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  • $\begingroup$ Thanks Klaus! That helps. I will explore that. Would you expect this to form as a side product? i.imgur.com/9hDnzzv.png $\endgroup$ – curious_cat Apr 7 '16 at 17:58
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    $\begingroup$ @curious_cat No, not really. If I remember correctly, the transformation is was regioselective on geraniol derivatives, but the yields differed a lot, depending on the kind of derivative (acetate, sulfone, thiophenyl ether) used. You might want to run a search with the keywords Sharpless allylic oxidation, selenium dioxide, and geranyl acetate to find some more reliable references. Quite often, the reaction is performed with catalytic amounts of $\ce{SeO2}$ and tert.-butyl hydroperoxide. $\endgroup$ – Klaus-Dieter Warzecha Apr 7 '16 at 19:06

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