[asdaf7477]

Dear Chemists,

I have been scratching my brain at this problem, would anyone kindly help with the retrosynthetic analysis as well as the forward enantioselective synthesis of a molecule. I can't upload the Chemdraw version of it, and I can't fin the molecule on-line, here is one close enough to it, change the subtituents to the ones below:

http://www.bmrb.wisc.edu/metabolomics/standards/D_glucono_1_5_lactone/lit/3498.png

Note that the Carbonyl is referred to as at position 1, the oxygen in the ring is at position 2 and so on clockwise.
redraw the molecule so that the following is the structure:
- At position3, a backward facing CH₂)OH group as well as a forward facing H
- At position 4 and 5 2H on each cabon
- At position 6 there are two groups, one is a forward facing Methyl group, and the second is a backward facing CH₂Ph group.

Sorry if this is a little confusing, my Chemsketch isn't uploading for some reason. I will try again tonight, if it work I will re-post this

Thank you for reading!

[zengjia1029]

As you defined, the structure must be as below:

[asdaf7477]

yes thank you!!!

[zengjia1029]

My synthesis route. Any comments, thanks in advance.

[asdaf7477]

wow thank you so much! I will need some time to absorb this in, if i have any questions i'll let you know

[StarvinMarvin]

Just by quickly looking at the scheme:

first reaction needs Cu to facilitate 1,4 addition, doesn't it?

[zengjia1029]

Just by quickly looking at the scheme:

first reaction needs Cu to facilitate 1,4 addition, doesn't it?

You are right! I have made a mistake. bisallyl copper lithium always go through a 1,4 addition.

[mirro]

In step 2 of your Evans aldol reaction, i think you need to add a base like DIPEA to form the enolate, and I wonder if it works stereoselective with an electrophile like BnBr.

I think the product of your last reaction will be this: