[beardy]

Useful. Thanks for the sight. Just realized the proposed starting compound (diene) wouldn't be accepted for the project because it's more than 4 carbons in a chain  We can only use 4-carbon chain or less

[kriggy]

SHouldnt there be one more double bond after the diels alder reaction?

[Shadow]

D'oh!

[Shadow]

I modified the synthesis:

-the product from the condensation with methyl glyoxal, can be reduced with H₂ to the molecule with one double bond

[beardy]

We just covered amines. I'm surprirsed that the arndt-eistert reaction wasnt mentioned. Quite useful

[beardy]

I modified the synthesis:

-the product from the condensation with methyl glyoxal, can be reduced with H₂ to the molecule with one double bond

I underwent the mechanism for this reaction and came to an 1,2-diol intermediate. After toying with possible mechanisms beyond this point, I wasn't able to reach the proposed condensation at beta position.

[beardy]

Forgive my stubbornness. Still working with the beta lactone as my starting reactant. Installed TMS group in place of malonic anhydride.

[orgopete]

In step one, methoxide will open the lactone.

[beardy]

Thanks for the notice, revised.

[Shadow]

I modified the synthesis:

-the product from the condensation with methyl glyoxal, can be reduced with H₂ to the molecule with one double bond

I underwent the mechanism for this reaction and came to an 1,2-diol intermediate. After toying with possible mechanisms beyond this point, I wasn't able to reach the proposed condensation at beta position.

The two hydroxyl groups will be eliminated by an E1cB mechanism and you will get a conjugated diene. Maybe subsequent hydrogenation won't work as well as I thought.

[orgopete]

I modified the synthesis:

-the product from the condensation with methyl glyoxal, can be reduced with H₂ to the molecule with one double bond

I underwent the mechanism for this reaction and came to an 1,2-diol intermediate. After toying with possible mechanisms beyond this point, I wasn't able to reach the proposed condensation at beta position.

Why won't the Claisen product (cyclopentanedione) form?

[Shadow]

Because methyl glyoxal is far more electrophilic.

[orgopete]

But it will form more enolate and can form a five member end ring on addition to the ester. Try drawing your intermediate aldol product and look at all enolate reactions. A Claisen product is more acidic and will lead to a more favorable acid anion.