I moved this discussion from the "Wanted References" thread in Novel Discourse, as that thread is for requests only, and below the posts made by Antoncho and hest has been reiterated, as well as all the mentioned articles I had access to has been linked to inline. /Rhodium
Posted by Antoncho:
Here's a humble request from two of our Hyperlab bees: Fomalhaut and Dionket. They are going to try synthesizing psylocybine in the upcoming weeks. Both having an extensive lab experience and an access to all the fancy reagents and equipment, i dare say they have a decent chance of succeeding at this - if they don't get too lazy to purify their intermediates, that issmile
However, they lack one crusial detail - 4-hydroxyindole or, to put it more precisely, a synthesis of such from more or less available reagents (on the pic beelow you'll see what they mean by 'more or less available'smile). They dug up a route to their precursor on the Chemical Abstracts, but the journal to which the abstract references isn't available to them.
Please, if somebee can find this article for them, do so! In case of either outcome the results of their experimentation promise to bee interesting.
J.M. Bobbit, Dutta, Journal of the Chemical Society, Chemical Communications 1968, 22, 1429.
Posted by hest
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000393684-file_sjqk.pl)
It should bee straightforward, start with some analogue of salisylaldehyde (the benzyloxy?) Make the synth, deprotect and make the acetate.
I think we could use a psilocybin synth here, growing mussies is too slow
Some refs:
Synth. Comm. 2077-2102 (1992) AND 186-188 (1995) (the indole synth)
Synthesis 935-938 (1999) (https://www.thevespiary.org/rhodium/Rhodium/chemistry/psilocybin.html)
(https://www.thevespiary.org/rhodium/Rhodium/chemistry/psilocybin.html)
J.Med.Chem. 4701-4710 (2000) (https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-fluorotryptamines.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-fluorotryptamines.pdf)
Organic Syntheses, CV 7, 34 (http://www.orgsyn.org/orgsyn/prep.asp?prep=cv7p0034)
(http://www.orgsyn.org/orgsyn/prep.asp?prep=cv7p0034) (Found by Terbium)
JCS Chem Comm 22, 1429 (1968)
By J. M. Boitt and C. P. Dutta
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000393684-file_rt02.gif)
Condensation of a 1,3-cyclohexanedion with an aminoacetaldehyde in benzene and in the preseceof p-toluen-sulphon acid yealded after azeotropic destil of wather an oxo-amine.
treatment of this with cold 3M HCl gave the 4,5,6,7-tetrahydro4-oxo-indole. (app.50%). More concentrated acid gave a dimer.
Convertion to the indole has been done (W.A. Remers and M.J.Weiss JACS 87, 5262 (1965) (https://www.thevespiary.org/rhodium/Rhodium/pdf/4-indolol.cyclohexanedione.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/4-indolol.cyclohexanedione.pdf))
(There is no experimental in this article)