Trotsky
Hazard to Others
Posts: 166
Registered: 6-2-2013
Location: US
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
bfesser
Resident Wikipedian
Posts: 2114
Registered: 29-1-2008
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
solo
International Hazard
Posts: 3967
Registered: 9-12-2002
Location: Estados Unidos de La Republica Mexicana
Member Is Offline
Mood: ....getting old and drowning in a sea of knowledge
|
|
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)
This file has been downloaded 921 times
Attachment: Oxidative Friedel - Crafts Reaction and its Application to the Total Syntheses of Amaryllidaceae Alkaloids.pdf (267kB)
This file has been downloaded 412 times
It's better to die on your feet, than live on your knees....Emiliano Zapata.
|
|
|
Trotsky
Hazard to Others
Posts: 166
Registered: 6-2-2013
Location: US
Member Is Offline
Mood: No Mood
|
|
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?
|
|
|
bfesser
Resident Wikipedian
Posts: 2114
Registered: 29-1-2008
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
Trotsky
Hazard to Others
Posts: 166
Registered: 6-2-2013
Location: US
Member Is Offline
Mood: No Mood
|
|
Yeah. I wonder if it's possible to use a different compound in step 3 to form the dimethyl ethanamine.
|
|
|
Bronstein
Harmless
Posts: 41
Registered: 15-1-2007
Member Is Offline
Mood: No Mood
|
|
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]
|
|
|
Illegal Parkinson
Hazard to Self
Posts: 75
Registered: 2-10-2005
Member Is Offline
Mood: No Mood
|
|
dihydrojoubertiamine synthesis
yes, it looks like an interesting compound. Please keep me updated.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
