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Topic: Synthesis route  (Read 2296 times)

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Offline quantumnumber

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Synthesis route
« on: September 09, 2014, 06:07:41 PM »
Hi everyone,

could you check this synthesis? Does it look right? Too steric hindrance, maybe...

Thanks.
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Offline phth

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Re: Synthesis route
« Reply #1 on: September 09, 2014, 07:54:17 PM »
Why not start from benzil? Tert alcohol=>ketone.  And sterics will probably be a problem, how much of one? I dont know. could be problematic because of rearrangements, though.
« Last Edit: September 09, 2014, 08:05:29 PM by phth »
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Offline quantumnumber

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Re: Synthesis route
« Reply #2 on: September 10, 2014, 06:56:40 AM »
Quote from: phth on September 09, 2014, 07:54:17 PM
Why not start from benzil? Tert alcohol=>ketone.  And sterics will probably be a problem, how much of one? I dont know. could be problematic because of rearrangements, though.
Sorry, I don't get your point...
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Offline AlphaScent

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Re: Synthesis route
« Reply #3 on: September 10, 2014, 09:39:37 AM »
I dont think you can start from benzyl due to the carbonyl. 

The dithianes do funny umpolung things also.  This is tricky.  More thought needed.
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Offline phth

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Re: Synthesis route
« Reply #4 on: September 10, 2014, 04:11:39 PM »
c1ccccc1C(=O)C(=O)c1ccccc1+C1CCCC(=O)C1, but we could get a rearrangement to Ph2RCOH.  Sorry if I was not clear.
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Offline AromaticAcrobatic

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Re: Synthesis route
« Reply #5 on: September 11, 2014, 01:15:13 AM »
I agree, that grignard phenyl would not be pumped about trying to get into that tight spot. How about starting with 2-benzanonecyclohexanol throw a protecting group on the hydroxide, wittig using bromomethylbenzene as the primary alkyl hailde for your illiad, then anti-diol the alkene followed by chromic acid.


 :spinpaired:
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