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Topic: Stuck with Morphinan cyclization  (Read 2946 times)

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Offline lutesium

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Stuck with Morphinan cyclization
« on: August 25, 2010, 04:07:25 AM »
Dear Sir/Ma'am

I'm stuck with the cyclization / rearrangement of Morphinans!!!
Which Carbon comes over which Carbon??? 
Can you explain via numerating them???
How does Phosphoric Acid Catalyze this reaction!!!
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Offline orgopete

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Re: Stuck with Morphinan cyclization
« Reply #1 on: August 27, 2010, 12:10:00 PM »
As drawn, I would only predict formation of an ammonium salt. I see no reason to predict lost of H2. If there was an OH at the carbon in which the bond forms, then phosphoric acid might reasonably protonate the alcohol, form tertiary carbocation, form a bond ortho to the CH2 group, and rearomatize.
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Offline lutesium

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Re: Stuck with Morphinan cyclization
« Reply #2 on: September 11, 2010, 11:29:38 AM »
Thanks for your answer but I want to know exactly which Carbon atom comes over which???

Thanks again!!!
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Offline mehc

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Re: Stuck with Morphinan cyclization
« Reply #3 on: September 12, 2010, 01:28:20 AM »

Consult it

http://www.scs.illinois.edu/denmark/presentations/2006/gm-2006-01n31.pdf

On page 5, take (S)-norcoclaurine and salutaridinol as your mentioned starting material and product.

Hope it'll help.
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