[greenE]

Hi there,
I have a problem that I know very little about chemistry. Thus instead explaining you what I want to know it was easier to find a program and draw the hypothetical reaction.
There is a starting molecule and the one that I hope for.
Is this possible to be done? If yes how would you do it?

Yield is not a problem. Im more interested in mechanics and conditions for this to happen at first place.

Thanks

[opsomath]

It is really weird to me that you want to start with this complicated structure to make the alkene shown. If I wanted to make that structure, I would buy dirt-cheap 4-iodoanisole and allylmagnesium bromide and Kumada couple them.

Or start with an aldehyde and do a Wittig.

Or start with p-bromomethylanisole and add sodium acetylide, then reduce.

Or basically anything except use the starting material shown.

If you put a gun to my head and made me use that, I would use LAH to reduce the whole thing to a diol, make the aldehyde by periodate oxidation, then Wittig it with methyltriphenylphosphonium iodide. Dirty, sloppy, and effective.

Or...did you mean you want to make the thing on the left from the thing on the right? In that case you should use a retrosynthesis arrow, =>, and not the double arrows.

[Honclbrif]

1. LiAlH4
2. Corey-Winter

[greenE]

Hi opsomath,

Thank you for your prompt reply.

The arrows are pointing in the right direction. As I already stated. I know little about organic chemistry and in my head it wasnt supposed to be double arrow but multi step reaction.
I want to use that complicated molecule as starting point to get an alkene. Not the opposite.

The thing that I'm missing in your suggested scheme is that Wittig is generating a C-C bond. I dont want that.
Is your scheme including decarboxylation prior new double CC bond formation?

Is there any chance to do this without braking and rejoining C-C bonds?
Im interested in removing hydroxy and carboxy groups and forming a double bond in between those two C atoms.

[greenE]

1. LiAlH4
2. Corey-Winter

This looks like it might work but I have to read more about it.

[opsomath]

Honclbrif's response is better than mine. Go with that.

Mine oxidizes off one carbon, then puts it back on. Like I said, sloppy. On the other hand, all those reactions should be very reliable.

[greenE]

Honclbrif's response is better than mine. Go with that.

Mine oxidizes off one carbon, then puts it back on. Like I said, sloppy. On the other hand, all those reactions should be very reliable.

opsomath, I appreciate your help.

This is my thing. I'm a biologist (dont bail on me :-) with strong knowledge in directed evolution. Now what I want is to start evolving enzymes for the purpose to develop highly specific catalysts for the reactions that do not exist in the nature and in the same time to avoid using toxic solvents and catalysts.
This is on example of completely unnatural reaction that I wanted to try my chances with. Im not looking for the best solution but for inspiration. I would like to know what my enzymes need to do in step wise manner before I chose my candidates. As long as those reactions can yield some product its fine with me.

If you can give me any additional suggestion for this kind of "chemical transformation". Different reaction mechanisms. It would mean a lot to me.

[Doc Oc]

I think a-hydroxy acids will decarboxylate similarly to malonic ester if heat is applied.  Then you'd have the aldehyde after that.

[discodermolide]

I think a-hydroxy acids will decarboxylate similarly to malonic ester if heat is applied.  Then you'd have the aldehyde after that.

Decarboxylation of malonic acids requires a 6-membered transition state involving the acidic proton and the adjacent carbonyl group., this is not achievable in the case of an alpha hydroxy acid. In the case mentioned here I may expect elimination of water the give the phenyl acrylate, which is a nicely conjugated system

[greenE]

Thank you all for the input.