[curiouscat]

Is it possible to join the two molecules  shown below & make an ester out of it? What'd be the best strategy?

Also, which of the four -OH positions are most likely to esterify? Would making an acyl chloride help? Or transesterification?

[discodermolide]

Certainly the carboxylic acid will make the ester, probably better via the acid chloride. But which phenolic OH will react I can't say as there is not much between them. You will very likely get a mixture:(
The OH groups on the starting material may well be more reactive than the phenols:(

[curiouscat]

Certainly the carboxylic acid will make the ester, probably better via the acid chloride. But which phenolic OH will react I can't say as there is not much between them. You will very likely get a mixture:(

Thanks @disco! Even a mixture is OK for now.

The OH groups on the starting material may well be more reactive than the phenols:(

Unfortunately that's what seems to happen. Is there any way to avoid this? By reagent choice? By protection?

Alternatively, any way to activate any one of the four -OH groups (from the other molecule) that I would rather have react?

[curiouscat]

Any comments if I used these two molecules as the acid moeity instead? Still the same risk of internal esterification?

[discodermolide]

Yes, and perhaps anhydride formation as well.
Try it and see what happens.

[curiouscat]

Yes, and perhaps anhydride formation as well.
Try it and see what happens.

Ok, tried. With  the esterification works.

With it does not work but internal coupling seems to happen.

[discodermolide]

You using chiral shikimic acid?
Which phenol group, was esterified?

[curiouscat]

You using chiral shikimic acid?
Which phenol group, was esterified?

Working on it!

[Enthalpy]

What if you dilute the first reactant and concentrate the second? I imagine this would favour their common ester and reduce the reaction of the first reactant with itself.

Please forgive if I put nonsense, and sorry for interrupting.

[kriggy]

That is valid idea!
I read some literature about high dilution, they used it for favor the cyclization instead of polymerization it might work here.

Im getting a bit lost here. You are using the shikimic acid to make an ester with the those compounds?