Any chemists here? organic chemists in particular
I have a dicyclic ketone compound with a hydroxyl group on it and I want to do a Wolff-Kishner reduction reaction to reduce both ketones to alkanes but would a Wolff-Kishner reduction affect the OH group in anyone because I want to keep the OH group on the compound unreacted
What drug is this?
>>7665485
Why do you need to know what drug this is?
>>7665482
Wolff Kishner does not reduce alcohols, I never actually used that in practice but I believe it uses an alcohol as a solvent.
Don't know how much it costs either. You can always go the gay route and dehydrate and hydrogenate
>>7665491
Ok thanks, good to know
also lol no gay routes here
>>7665495
What are you working on anon
OP here,
stayed tuned I'll keep you guys updated and may need some more advice
>>7665526
u makin nerve agents?
>>7665572
Do I look like the scarecrow?
>>7665529
hey faggot, Andrew Myers lab published a modified Wolff-Kishner using TBS-hydrazones that goes under more mild conditions
http://faculty.chemistry.harvard.edu/files/myers/files/108_2004_furrow_jacs_126_5436.pdf?m=1396661110
shit guys, I need to make a dicyclic structure more reactive to bond with a michael acceptor
any ideas?
Maybe a diels-alder reaction?
>>7665585
By the way, that's cool but I dont really have a need for a silylhydrazone
I need to install some cyclic compounds on this michael acceptor but then I need the alkene bond back, so I need a compound with a good leaving group and i'll have to work under basic conditions i guess so I can deprotonate this stupid thing
>>7665611
Post the damm reaction
>>7665614
Can I draw on here?
>>7665614
Im not posting the entire synthesis anon
help
How do I attach these cyclic structures? What carbon chains do I use
>>7665683
Just to add, I've made the dicyclic structures you see on the right, and I know how to reduce the ketones
bump
I need help with a synthesis for a secondary metabolite
>>7665683
This is *never* going to work as drawn.
Something simpler (not OP): what's the mechanism for this shit? I'm ill and even shitposting on /sci/ is too much effort. I don't need the drawn mechanism, just some guideline about where to start.
>>7667236
This involves the pinacol rearrangement mechanism. First, one of the hydroxyls is protonated by a strong acid. Next comes a rearrangement involving the other hydroxyl which forms a carbonyl and pushes out a water molecule.
>>7667247
Thank you, anon. Saved my day.
