[Ariana]

Please see attached file.

You can only use starting materials of 4 carbons or less for the transformation.

Any type of help/hints/ideas will be appreciated =].

[Borek]

Please read forum rules.

[Ariana]

Read. I suppose you're asking me to show an attempt at the problem?

Please see attached file again. I get the bottom part alright. I'm just confused about incorporating the top part -__-. And if there's a different way to do this. etc

[AWK]

The method with BH₃ will not work in this case

[Ariana]

Aah yea. I must have been sleepy when doing that =P. Anyway, here's the solution. There's only a slight problem at step 10 where an anti-markovnikov addition should be done instead of the ROOR and HCl (which causes radical formation). The OH should be replaced with either a Cl, Br.

[kiwi]

the Freidel-Crafts acylation wouldn't give the product you've drawn; can you see why?

[Heory]

See the synthetic route as follows.

[Ariana]

the Freidel-Crafts acylation wouldn't give the product you've drawn; can you see why?

Not really o_O. Are you talking about step 7? Wouldn't it attach to the benzene at ortho or meta position?

See the synthetic route as follows.

Wow. Thanks. It's much simpler. Though, I haven't used the reagent PPA before. Still *thumbs up*

[nj_bartel]

Hint about the Friedal Crafts - aluminum chloride has an empty p-orbital, which makes it a...?

[kiwi]

Not really o_O. Are you talking about step 7? Wouldn't it attach to the benzene at ortho or meta position?

Getting there - there are multiple problems with the step as drawn. Have a bit of think about the different reagents and functional groups in the SMs and product