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Mechanism of Retrosynthesis

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Ferny:
Guys, I urgently need the retrosynthesis mechanism of this synthesis that I found in a paper. I don't know how to start. Could someone help me with the mechanism, including the triazole addition part?


Thank you very much!

wildfyr:
So two of these reactions not always studied in sophomore organic chemistry, though one is a branch of chemistry you do know.

I'm not going to push arrows for you, but I'll help you with some vocabulary to help you google and wikipedia your way.

step 1 is the formation of an activated ester from a carboxylic acid a carbonyl diimidazole (an intermediate, not isolated).  Converting product 4 into product 5 is a williamson ether synthesis. This is followed by a combined aldol condensation of the ketone and the benzylic position of the ester to make an enone, and also the reaction of the phenol with the (other) activated carbonyl to make an ester. That's the trickiest part, try drawing it out.

The third reaction is a copper click reaction, also known as CuAAC. Its a fantastic reaction only invented in the last 20 years. Its a copper catalyzed version of Huisgen cycloaddition.

Ferny:

--- Quote from: wildfyr on November 21, 2023, 06:36:50 PM ---So two of these reactions not always studied in sophomore organic chemistry, though one is a branch of chemistry you do know.



I'm not going to push arrows for you, but I'll help you with some vocabulary to help you google and wikipedia your way.

step 1 is the formation of an activated ester from a carboxylic acid a carbonyl diimidazole (an intermediate, not isolated).  Converting product 4 into product 5 is a williamson ether synthesis. This is followed by a combined aldol condensation of the ketone and the benzylic position of the ester to make an enone, and also the reaction of the phenol with the (other) activated carbonyl to make an ester. That's the trickiest part, try drawing it out.

The third reaction is a copper click reaction, also known as CuAAC. Its a fantastic reaction only invented in the last 20 years. Its a copper catalyzed version of Huisgen cycloaddition.

--- End quote ---

@wildfyr

Thank you so much to help me with this vocabulary. I'm really new in organic chemistry in college, but this question is the final question to close my semester.

After do the mechanism you described, the original Synthesis. Do i only need to do the reverse way to get the retrosynthesis reactions or the mechanism is different?

rolnor:
I gave you a molsnack wildfyr

Ferny:

--- Quote from: wildfyr on November 21, 2023, 06:36:50 PM ---So two of these reactions not always studied in sophomore organic chemistry, though one is a branch of chemistry you do know.

I'm not going to push arrows for you, but I'll help you with some vocabulary to help you google and wikipedia your way.

step 1 is the formation of an activated ester from a carboxylic acid a carbonyl diimidazole (an intermediate, not isolated).  Converting product 4 into product 5 is a williamson ether synthesis. This is followed by a combined aldol condensation of the ketone and the benzylic position of the ester to make an enone, and also the reaction of the phenol with the (other) activated carbonyl to make an ester. That's the trickiest part, try drawing it out.

The third reaction is a copper click reaction, also known as CuAAC. Its a fantastic reaction only invented in the last 20 years. Its a copper catalyzed version of Huisgen cycloaddition.

--- End quote ---

With your help, i could draw the mechanism of the direct synthesis! Thanks!

Now, to do the retrosynthesis mechanism, do i need to only do the reverse path and show the interconversions and decouplings in the molecules?

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