Uploaded June 2022 | Updated September 2026, 3 weeks ago
In this video, I discuss some of the interesting mycotoxins produced by mushrooms!
patreon.com/thatchemist
Community Discord - discord.gg/QWNPETtPcZ
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Links to articles discussed in this episode:
Tinky Winkenic Acid discovery - doi.org/10.1038/nchembio.179
Illudins - doi.org/10.1016/S1568-7864(02)00166-0
Ibotenic Acid - doi.org/10.1007/BF03159956
Muscimol - doi.org/10.2174/1568026023393525
Coprine - doi.org/10.1124/pr.111.005538
Coprine - ISBN 0-7167-2600-9
Muscarine - doi.org/10.1080/15563650903008448
Psilocybin & Psilocin - doi.org/10.1080/1355621021000005937
Orellanine - doi.org/10.1093/ndt/14.11.2779-a
Agaritine - doi.org/10.1080/02652030210156340
Agaritine carcinogenicity - doi.org/10.1016/0278-6915(94)00142-B
Amatoxins - doi.org/10.1007/BF00444032
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0:00 Introduction
0:07 Wild Mushrooms are Dangerous!!! . You should never consume random mushrooms
0:43 Triangulenic Acid (Tinky Winkenic Acid) . This toxin is found in Russula subnigricans
2:50 Ibotenic Acid & Muscimol . One of the most famous mushrooms - Amanita Muscaria
3:36 Coprine . Present in Coprinopsis atramentorio (the common ink cap)
5:43 Psilocybin & Psilocin . Famously know in mushrooms from the genus Psilocybe (magic mushrooms)
6:41 Orellanine . From the Orellani-e.g. Cortinarius rubellus (deadly webcap)
8:31 Amatoxins • Notably present in Amanita phalloides (the death cap) . The red substituents vary between amatoxins
In this video, I discuss some of the interesting mycotoxins produced by mushrooms!
patreon.com/thatchemist
Community Discord - discord.gg/QWNPETtPcZ
----------------------------------------------------------------------------------------------------------------------------------
Links to articles discussed in this episode:
Tinky Winkenic Acid discovery - doi.org/10.1038/nchembio.179
Illudins - doi.org/10.1016/S1568-7864(02)00166-0
Ibotenic Acid - doi.org/10.1007/BF03159956
Muscimol - doi.org/10.2174/1568026023393525
Coprine - doi.org/10.1124/pr.111.005538
Coprine - ISBN 0-7167-2600-9
Muscarine - doi.org/10.1080/15563650903008448
Psilocybin & Psilocin - doi.org/10.1080/1355621021000005937
Orellanine - doi.org/10.1093/ndt/14.11.2779-a
Agaritine - doi.org/10.1080/02652030210156340
Agaritine carcinogenicity - doi.org/10.1016/0278-6915(94)00142-B
Amatoxins - doi.org/10.1007/BF00444032
----------------------------------------------------------------------------------------------------------------------------------
0:00 Introduction
0:07 Wild Mushrooms are Dangerous!!! . You should never consume random mushrooms
0:43 Triangulenic Acid (Tinky Winkenic Acid) . This toxin is found in Russula subnigricans
2:50 Ibotenic Acid & Muscimol . One of the most famous mushrooms - Amanita Muscaria
3:36 Coprine . Present in Coprinopsis atramentorio (the common ink cap)
5:43 Psilocybin & Psilocin . Famously know in mushrooms from the genus Psilocybe (magic mushrooms)
6:41 Orellanine . From the Orellani-e.g. Cortinarius rubellus (deadly webcap)
8:31 Amatoxins • Notably present in Amanita phalloides (the death cap) . The red substituents vary between amatoxins

![Dithioles - A Universal Scaffold for Organic Synthesis (Important Papers)
As there is no comprehensive reviews anywhere which showcase the versatility of these reagents, I decided to spill the beans on some of the best chemistry out there.
In this video, I share what is arguably the most versatile building block in organic synthesis - the dithiole. Its like a Corey dithiane but way easier to manipulate - need to make a carbonyl? Simply use Ag2O. Want a CH2? Use Raney nickel. Mild bases can be used once you start oxidizing the dithiole to the sulfoxide(s) and sulfone forms, meaning that they can readily be alkylated or coupled with various electrophiles. You can also make them react as carbenes (from the 2-chloro-sulfone, for example)!
Interested in synthetic consulting? Get in touch! More info at the end of the video. Interested sponsors are also encouraged to reach out.
Important Papers covers various chemical reactions, mechanisms, and research papers in the field of organic chemistry, providing examples and explanations for each research paper.
Support the Channel on Patreon - https://www.patreon.com/thatchemist
Important Papers Playlist - https://youtube.com/playlist?list=PL6OLqxmk7RtyRkdJhXK8NWpT1krGNq1p4
References:
Huge BDT review (1985; featuring some stuff which wasnt discussed here) - https://doi.org/10.1080/01961778508082475
Dioxygenase ref 1 - https://pubs.acs.org/doi/10.1021/ja00049a004
Dioxygenase ref 2 - https://doi.org/10.1016/j.tet.2003.10.107
dithiole oxidation to sulfoxide, sulfone, and carbene chem - https://doi.org/10.1016/S0040-4020(01)90393-X
Dithiole monosulfoxide chlorination - https://doi.org/10.1055/s-1985-31261
Lithiation of dithiole with trapping by aldehydes and ketones - https://doi.org/10.1016/j.tet.2003.10.107 (the dioxygenase paper)
Another aldehyde/ketone paper which I dont have the DOI of - Brown, Charles Allan; Chapa, O.; Yamaichi, A.[Heterocycles, 1982, vol. 18, p. 187 - 189]
Fluorination of the dithiole bis-sulfone with selectfluor - https://doi.org/10.1002/anie.200906866
N-parameters of bis-sulfone and fluoro bis-sulfone (they dinked up the figure and had to submit a correction btw) - https://doi.org/10.1002/anie.201605616
1,2- and 1,4- substitution of the fluoro bis sulfone - https://doi.org/10.1002/anie.200906866
Eeros BDT-BF4 - https://doi.org/10.1002/047084289X.rb027
Tributyltin hydride on the BDT ether and amines - https://pubs.acs.org/doi/10.1021/jo00003a052
Adding in the mono sulfoxide into nitroarenes - https://doi.org/10.1080/10426509308036881
imine scandium triflate cyclization - https://pubs.acs.org/doi/10.1021/ol020179d
chloro bis-methyl acetal dithiafulvalene synthesis from dithiol - https://doi.org/10.1002/jhet.5570310676
intramolecular domino cyclization of dithiafulvalene (aka EAS reaction) - https://doi.org/10.1021/jo00304a021
^paper also discusses the chemoselective transformations from slide 30
indole functionalization of DMBDT, difluoroether synthesis, radiofluorination, etc - https://doi.org/10.1002/chem.202202862
My PhD thesis New Fluorination Strategies and Reagents -
https://summit.sfu.ca/item/37816
Trityl BF4 synthesis - https:doi.org/10.1055/s-1972-21914 (the other ways using carboxylic acid anhydrides suffer from purification issues - it is easier to do it this way if you dont hate yourself)
Eeros Trityl BF4 Review - https://doi.org/10.1002/047084289X.rt362.pub2
TTF/DTF article 1 - https://link.springer.com/article/10.1007/s007060200074
TTF/DTF article 2 - https://doi.org/10.1002/chem.201802744
Dear materials scientists, please make 1 product with dithiafulvalenes or tetrathiafulvalenes by 2030, otherwise the organic chemists will think you are clowning
MW Dictionary - Fraud (Noun)
Synonyms of fraud
: deceit, trickery
specifically : intentional perversion of truth in order to induce another to part with something of value or to surrender a legal right
: an act of deceiving or misrepresenting : trick Dithioles - A Universal Scaffold for Organic Synthesis (Important Papers)](https://i.ytimg.com/vi/vLjEdrvji3c/mqdefault.jpg)








