[dikapmn]

Anyone can help me to know how to synthesis this molecule?

I think of this with grignard and ketone.

But I don't know how to put the alcohol to the cyclohexane.
Or is it another possible way to synthesis it with the real existing molecule and reagent in this world?
Sorry for my english.

[kriggy]

Im not sure but I think the last reaction is impossible. But, what if you used different grignard reagent in the 1st step?

[Rutherford]

Transform the left part OH to ketone and the right one OH to double bond. Asymmetric reduction of the left ketone and protection of the obtained alcohol followed by Sharpless asymmetric dihydroxilation with subsequent transformation to an epoxide and ring opening of the epoxide with organolithium would afford the product.

[dikapmn]

Transform the left part OH to ketone and the right one OH to double bond. Asymmetric reduction of the left ketone and protection of the obtained alcohol followed by Sharpless asymmetric dihydroxilation with subsequent transformation to an epoxide and ring opening of the epoxide with organolithium would afford the product.

thanks for the answer.
What molecule I used as precursor? and what reagent that I use to give that target molecule?

[Rutherford]

4-Vinylcyclohexyl-methylketone

[dikapmn]

4-Vinylcyclohexyl-methylketone

Thank you so much!
But can you give me some picture of the reaction, please. No need for the mechanism, just to make sure of my work.
Thanks again

[kriggy]

Im not realy sure if the method suggested by rutheford will work, I dont see how the epoxide would open in the way its required for the target molecule


I suppose you could convert the double bond into hydroxide, oxidize it into ketone and then use addition of organometalic reagent to form the alcohol you desire

[Rutherford]

4-Vinylcyclohexyl-methylketone

Thank you so much!
But can you give me some picture of the reaction, please. No need for the mechanism, just to make sure of my work.
Thanks again

Here you are (TM=target molecule):

One note: I have mistaken and reduced the side chain with the ketone group by one carbon atom, but the reaction selectivity won't change at all.

[dikapmn]

Thank you so much kriggy and Rutherford for helping me.
You're so clever!

[kriggy]

Hm interesting, guess chemdraw got me wrong structure of the starting material then makes sence now