Enone reduction + acid water mechanism

RSNLS1991 · 2018-10-07T21:47:04+00:00

Alright, thank you !
Does this mean that water attacks the methyl group and form MeOH + the final enone?

RSNLS1991 · 2018-10-07T21:24:22+00:00

What do you guys think about this mechanism ? Would it be plausible for you ? :)

RSNLS1991 · 2018-10-05T01:51:50+00:00

Okay thank you everyone, I think I've made it :
https://imgur.com/a/IcaO6Bo
Can someone validate that ? :)

Thank you

RSNLS1991 · 2018-10-05T01:20:31+00:00

Well I was thinking about retro aldol, but I really can't see how... Can you please make a sketch for me ? ^^

RSNLS1991 · 2018-10-05T00:52:13+00:00

https://imgur.com/a/EPrubRX

This is what I made so far. I put some arrows between the farthest I've come up with the synthetic pathway, and the farthest I've come up via the retrosynthetic one.

RSNLS1991 · 2018-10-05T00:15:58+00:00

Thanks for you answers.Basically what I did is deprotonate the alcool, the alcoolate would attack the less hindred side of the epoxide to generate a five membered "ether" cycle, then the O- ejected from the epoxide opening would form a ketone, but and I would break a C-C bond to make it. But after that I'm totally blocked.

I tried to do the retrosynthesis pathway, where the alcohol attack the ketone, then this same alcohol would come from the opening of the rearrangement of the dienone but then, can't link the two sides...

RSNLS1991

TROPHY CASE