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Topic: Retrosynthetic Analysis  (Read 9250 times)

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Offline nayeee1m

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Retrosynthetic Analysis
« on: March 10, 2016, 11:37:59 PM »
Can anyone Help me to do retrosynthetic analysis of this compound?
nayem

Offline Dan

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Re: Retrosynthetic Analysis
« Reply #1 on: March 11, 2016, 02:45:12 AM »
Nasty one!

Can you show what ideas you have come up with? Showing you have attempted the question is a Forum Rule.
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Offline clarkstill

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Re: Retrosynthetic Analysis
« Reply #2 on: March 11, 2016, 05:47:18 AM »
That is horrible! Also, a lot of undefined stereochemistry...

Offline orgopete

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Re: Retrosynthetic Analysis
« Reply #3 on: March 11, 2016, 03:22:23 PM »
This problem will require a little help, we missed the class in which it was assigned. What chemistry was being covered, heterocycles, asymmetric induction, etc, etc. I'm presuming the expected answer uses the chemistry being discussed, but we don't know what it is.
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Offline Arkcon

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Re: Retrosynthetic Analysis
« Reply #4 on: March 11, 2016, 04:16:33 PM »
Can you name this product for us?  Maybe using a name given in class,so we can know the stereochemistry?
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline critzz

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Re: Retrosynthetic Analysis
« Reply #5 on: March 11, 2016, 08:55:23 PM »
This molecule seems too advanced for an ordinary college exercise, or is it just me? I would really have to sit down to produce something plausible, especially because of the lack of oxygen atoms (even disregarding the stereochemistry).  :P

Offline BRSM

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Re: Retrosynthetic Analysis
« Reply #6 on: March 11, 2016, 09:18:39 PM »
Can you name this product for us?  Maybe using a name given in class,so we can know the stereochemistry?

I ran it through Scifinder and Reaxys for my own edification, and it's not a known compound. Guess it was made up for class.

At first glance it's a tough nut to crack, but there are a few conspicuous functional groups. You must have some ideas for the cyclohexene, piperidine and pyridine?

Really you only need one part you know how to make to start a retro!

Offline Rutherford

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Re: Retrosynthetic Analysis
« Reply #7 on: March 12, 2016, 05:33:32 AM »
Add some carbonyl group here or there and the number of possibilities is vast.

Offline nayeee1m

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Re: Retrosynthetic Analysis
« Reply #8 on: March 19, 2016, 01:46:05 AM »
 I come up with some analysis. Please can you help me with this :
nayem

Offline nayeee1m

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Retro-synthetic Analysis
« Reply #9 on: March 19, 2016, 01:51:19 AM »
Can anyone Help me to do retro-synthetic analysis of this compound ? I Just tried to break. Please help me out 
« Last Edit: March 19, 2016, 02:17:05 AM by nayeee1m »
nayem

Offline phth

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Re: Retro-synthetic Analysis
« Reply #10 on: March 19, 2016, 02:01:50 AM »
You could do some metal process for the first allylic alcohol.  OAc would serve as a protecting group or the allylic metal species.  Or use a allyl chloride.  You could do a reductive amination instead of working with a primary chloride.  Seem like you are missing a carbon for the last disconnection.  Which bond(s) connected to the pyridine ring would be the best to form first/second/thrid..?

Offline nayeee1m

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Re: Retrosynthetic Analysis
« Reply #11 on: March 19, 2016, 02:04:48 AM »
Lot of you asked to tell me name of this compounds. Unfortunately , this compound made by Professor in paper, does not exist.  I have show to retrosynthetic analysis. Please help me out. I cant do this myself. Need help from you guys
nayem

Offline nayeee1m

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Re: Retro-synthetic Analysis
« Reply #12 on: March 19, 2016, 02:06:38 AM »
Ya, you are right. I missed one carbon in last step. You also right from Alcohol protecting group. I noted down . Thanks I dont know answer yet for "Which bond(s) connected to the pyridine ring would be the best to form first/second/thrid..?"
nayem

Offline phth

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Re: Retro-synthetic Analysis
« Reply #13 on: March 19, 2016, 02:23:23 AM »
I think we got a pretty decend way to break down the macrocycle.  Next is can we break down the ring connections to figure out maybe a better way from where we have gotten so far, or a better way starting from another disconnection.  Answering the question I asked will address this problem. Where could you look to figure out the answer? What do you know about aromatic substitution reactions?

Offline Alwin Kristen

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Re: Retrosynthetic Analysis
« Reply #14 on: March 19, 2016, 03:49:52 AM »
Let us learn to dream, we then might find the truth. - F. A. Kekulé

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