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Author: Subject: dihydrojoubertiamine synthesis
Trotsky
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[*] posted on 8-7-2013 at 17:33
dihydrojoubertiamine synthesis


Dihydrojoubertiamine is a direct precursor to mesembrine in Sceletium joubetii and probably all mesembrine containing plants.

It has not been assayed for biological activity, which makes me interested.

there is a published synthesis, I think from 1973 but I'd like to know if there is a better or cheaper route.

The IUPAC for this compound would be 1-(4-hydroxyphenyl)-N,N-dimethylethanamine-cyclohexan-4-one. Okay that might not be IUPAC approved naming...

The structure can be found here, page 22: http://books.google.com/books?id=LXIV5N89TC8C&pg=PA22&am...

I'm actually more interested in the 3-hydroxy isomer of this compound than the natural 4-hydroxy.

any help would be awesome!

[Edited on 7/9/13 by bfesser]
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bfesser
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[*] posted on 8-7-2013 at 17:47


4-[2-(dimethylamino)ethyl]-4-(4-hydroxyphenyl)-cyclohexanone
<a href="http://www.guidechem.com/dictionary/28513-25-9.html" target="_blank"><img src="http://img1.guidechem.com/chem/e/dict/90/28513-25-9.jpg" /></a> <img src="../scipics/_ext.png" valign="top" />

[Edited on 10.1.14 by bfesser]




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solo
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[*] posted on 8-7-2013 at 18:36


Reference Information


THE AMARYLLIDACEAE ALKALOIDS .pdf
http://filecloud.io/z6q1th7j

Oxidative Friedel - Crafts Reaction and its Application to the Total Syntheses of Amaryllidaceae Alkaloids.pdf

Double Reduction of Cyclic Aromatic Sulfonamides- Synthesis of(+)-Mesembrine and (+)-Mesembranol.pdf

Attachment: Double Reduction of Cyclic Aromatic Sulfonamides- Synthesis of(+)-Mesembrine and (+)-Mesembranol.pdf (315kB)
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Attachment: Oxidative Friedel - Crafts Reaction and its Application to the Total Syntheses of Amaryllidaceae Alkaloids.pdf (267kB)
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Trotsky
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[*] posted on 10-7-2013 at 22:36


I actually need the meta-OH isomer. I realize it can be made from 4-desmethoxy-mesembrine, but there that's not exactly widely available. Would it be possible to follow a route similar to one used for ketamine?

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bfesser
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[*] posted on 11-7-2013 at 06:03


Are you referring to this route to <a href="http://en.wikipedia.org/wiki/Ketamine" target="_blank">ketamine</a> <img src="../scipics/_wiki.png" />:
<a href="http://en.wikipedia.org/wiki/Ketamine#Synthesis" target="_blank"><img src="http://upload.wikimedia.org/wikipedia/commons/d/db/Ketamine_synthesis.svg" width="600" /></a> <img src="../scipics/_wiki.png" />

[Edited on 7/11/13 by bfesser]




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Trotsky
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[*] posted on 11-7-2013 at 14:43


Yeah. I wonder if it's possible to use a different compound in step 3 to form the dimethyl ethanamine.
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[*] posted on 12-7-2013 at 01:16


Perhaps something like this would work?
(My chemistry program crashed while exporting this so some labels are missing, but I guess you can understand anyway.)

For a similar reaction as the second step, alkylation of a phenylacetone see Us patent 2281956, http://www.freepatentsonline.com/2281956.html.

The next to last step is a wolf-kishner reduction of the ketone, and the last step is a hydrolysis of the ketal. In the end you end up with the O-methyl version, I don't know if the remaining ketone would tolerate a cleavage of it with HBr? Otherwise you could use some other protection group, like benzyloxy.

But I think working out all the details of something like this would take some time, so perhaps best to go with something published...





[Edited on 12-7-2013 by Bronstein]
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[*] posted on 10-1-2014 at 11:50
dihydrojoubertiamine synthesis


yes, it looks like an interesting compound. Please keep me updated.
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