Synthesis of a molecule

[Martel89]

I need help coming up with the synthesis of the molecule attached below. I keep trying it, but I cant get it to work out, do you guys have any tips suggestions on how to solve this.

 

All of the carbon atoms come from alcohols that contain 4 carbons or less, that includes any bromides, grignards, wittig reagents etc.

 

thanks

[Mr Skeptic]

Unfortunately, solving this for you won't help you. I can almost guarantee that a similar (but almost certainly different) synthesis will appear on your test.

 

Try to break it down as much as you can. You need at least two reactions that add carbons. Which do you want to do first, and if it matters, why?

[mississippichem]

I won't flat out give you an answer, and there are many. Here's a hint to one of them:

 

Cut the molecule at the double bond, then think phosphorus.

 

That will lead you to a first step in your retrosynthesis.

 

 

Edit: forgot to add last sentence

Edited August 15, 2010 by mississippichem

[d_bakalov]

http://en.wikipedia.org/wiki/McMurry_reaction

You just need one ketone and one aldehyde with proper structure

[BurningKrome]

Hey...I'm not the one who asked the question...but, after studying the McMurray reaction, I'm still unsure about the electron movement during this particular reaction.

 

I wonder if someone could generate a mechanism document with the electron pushing arrows for this. You can send it to me via email if you don't want to spoil the asker's training When I try to figure it out from the Wikipedia diags and from the diags at http://www.organic-chemistry.org/namedreactions/mcmurry-reaction.shtm I keep ending up with a lone pair not accounted for.

 

Thanks!