[danmerqury]

I need to synthesize this compound, which, four steps later, leads to my final product. But I'm kinda stuck on how to get this. I'm assuming that starting from furan or THF would be the easiest way to go, but what would be the most efficient and easiest way to stick a methyl group and two double bonded oxygens on there?

[refid]

Would this work?

http://img296.imageshack.us/my.php?image=alphamethyltetronicacidhi1.jpg

Wondering if the carboxylic acid -OH can nucleophillic attack C-Br to close the ring

[kiwi]

Would this work?

http://img296.imageshack.us/my.php?image=alphamethyltetronicacidhi1.jpg

Wondering if the carboxylic acid -OH can nucleophillic attack C-Br to close the ring

it will as the Cs salt in DMF.

edit: that scheme won't work though. think about the chemoselectivity of the third step.

[refid]

Do you mean the water ester hydrolysis isn't a good route? I guess since it reversible... maybe base ester hydrolysis (saponification)...

[kiwi]

Do you mean the water ester hydrolysis isn't a good route? I guess since it reversible... maybe base ester hydrolysis (saponification)...

no sorry miscounted the number of steps, i mean the bromination will not give the drawn product

[sjb]

Do you mean the water ester hydrolysis isn't a good route? I guess since it reversible... maybe base ester hydrolysis (saponification)...

no sorry miscounted the number of steps, i mean the bromination will not give the drawn product

How about instead of hydrolysing the ester to the free acid, ester deprotonation with a) NaH, then b) BuLi (important to do it that way round), then treatment with your favourite bromination conditions eg DBI / NBS / Br2 etc, then hydrolysis / cyclisation?

S

[refid]

how about this guy, would the -OH attack the ester & do an ester hydrolysis?

[Custos]

This method is worth a look: http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1959/81/i17/f-pdf/f_ja01526a046.pdf?sessid=6006l3

[Wisemanleo]

Could a DOM-type of reaction work in this case?