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Author Topic: Resolution of stereoisomers in tropane alkaloids?  (Read 3865 times)

Offline Limpet chicken

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Hey, I need some help on this one.

How would I go about seperating tropane alkaloids extracted from plant matter (atropa belladonna), First, seperating out scopolamine, hyoscine, and hyoscyamine, then I need to resolve the resulting mixed atropine/tropine, if it helps, atropine is the more sterically hindered isomer of the two.

I am in need of pure atropine, and purified tropine for some experiments, regarding oxidation to tropinone, and have been unable to find any help on the matter:(

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Offline Ylide

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Re: Resolution of stereoisomers in tropane alkaloids?
« Reply #1 on: 12/12/2004 04:17:55 »
Well, if you're stuck with a mixture of tropine and atropine, getting pure atropine isn't that hard.  Tropine and tropic acid (synthesized pretty easily from phenylacetic acid) react with heat and HCl to form atropine.  This is then a simple purification to get your atropine.  

Atropine could be broken down into tropine and tropic acid by breaking the ester linkage, but I'm not sure if any of the reactions that do this would react with the rest of the structure.  

Your easiest solution might be chromatographic separation.  



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Offline Limpet chicken

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Re: Resolution of stereoisomers in tropane alkaloids?
« Reply #2 on: 12/12/2004 16:42:40 »
Interesting.

Do you have any references to the synthesis of tropine from phenylacetic acid, as that would make a convenient starting point, rather than going to the trouble of messing about seperating mixed plant alkaloids and waiting for plant growth in the first place:)

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Offline Ylide

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Re: Resolution of stereoisomers in tropane alkaloids?
« Reply #3 on: 13/12/2004 06:48:59 »
http://www.chm.bris.ac.uk/motm/atropine/synthesisch.htm

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Re: Resolution of stereoisomers in tropane alkaloids?
« Reply #3 on: 13/12/2004 06:48:59 »

 

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