[Ashbyd]

Hi guys, first time posting here. Yesterday while reviewing material for organic chemistry II, I came across a synthesis problem that completely stumped me.  I worked on it for a solid hour and a half, but I still can't figure it out. Here are pictures of the problem and my work so far:

Question:


Work:


If anyone could help me out, that would be amazing.

Thanks!

[Ashbyd]

I'm pretty sure I figured it out. I went in forward order this time to make it a little clearer. Here's what I've got.

[orgopete]

I can't say there wouldn't be any of the desired product in the gemisch that would result. It makes some of the connections, but I'd start by doing a symmetrical aldol to avoid the other possibilities that could occur if done at the end.

I think the enone can enolize in the correct direction as needed. Hopefully, this was discussed in your class at some point. You don't want the kinetic product.

I might convert the aldehyde into something else as I don't know how well it will undergo conjugate addition.