Question

Here is a molecule. Being asked to do a retro synthesis (reaction scheme) on the molecule and go all the way back to produce the molecule until I can't go back anymore (think benzene or carbon). I can use any source and synthesis/reaction to produce the molecule above. Some notes about the molecule:

H3CO

Here is my answer so far, I need help!

Please help, using my answer above here is what I noticed:

> Some steps can be omitted and rearranged.

> The first bromination and Wittig is unnecessary. Go ahead and show the same product via an aldol condensation (dimerization and water elimination) from cyclohexanone. I would also suggest that you perform the second aldol condensation inestad of doing the Wittig, otherwise you can't enolize.

> For the answer above you see that I did an aldol with a alkene as nucleophile, how do you think this should work, are protons alpha to alkene double-bond acidic?

Answer 1

Wittig / Grignard + detydzation. » cc formed by aldol condenca Hong formed by aldol addition ca bond c-o dis connection Ether tomation + old + 0-1+ NOO OH or opphe Aldol CG

FGI Har dehydontie 0 он <33 Aldo JL Aldol This combination OH is difficult to set up. so we have to take this as Starting material Cyclo hexanone

synthe six step-I -H dilute NOOH (CH₃)₂504 CH₂ I side reaction: Te you take conc. No off Cannizaro reaction will occur. cona RETH Nach och OCH step-Iio 1 AH NAOH Na Hao 11 CH

OH N. OHN acidic Na oH Bo 4 Co-

Step- - Br + pphz > =ppe = pphs OCH ap-phs opphz acou

ochy The overall reaction is Na oH o Na PPhy + o=ppha

Aldol by using alkene as nucleophile is not possible. Be cause ally lic protons are not that much a- pootone of Carbonyl acidic as compounds. more acidic thay alluce less acidic In Carbonyl compound, due to presence of electronegalive oxygen atom, group created electron defficiency at &-Carbon. so Hattato attatched to this a-c is acidic Y Bare of difficult difficult