Organic Chemistry Explained: Total Synthesis of Anti-Cancer Ginkgo Tree Molecule Bilobalide (Corey)
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- Опубліковано 10 чер 2024
- Dear organic chemistry peeps - today I am telling you the tale of the Ginkgo tree and dissect three different total syntheses of Bilobalide, a potential "anti-almost everything" molecule from the Ginkgo biloba tree (time-stamps below).
Even if you are not deeply engaged with total synthesis, I am confident that this video will enrich your understanding of chemistry and natural products to some degree.
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Show your support and interest by sharing a comment, liking the video and subscribing to my channel!
00:00 Introduction
00:56 Pls sub thx
01:25 Ginkgo biloba facts and biology
05:58 Corey's synthesis
10:06 Crimmins' synthesis
15:57 Ohtawa's and Shenvi's synthesis
Key papers:
- pubs.acs.org/doi/abs/10.1021/...
- pubs.acs.org/doi/abs/10.1021/...
- www.nature.com/articles/s4158... free access on ChemRxiv: chemrxiv.org/articles/preprin...
Some recommended books on organic synthesis:
- Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge)
- Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis)
- Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions)
- Nicolaou et al; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy)
- Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life)
- Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures) - Наука та технологія
psychedelics, or better known as the gateway drugs to organic chemistry.
I would really love to see Vanderwal's strychnine synthesis covered next because of it's sheer efficiency
Shockingly, just 10% of my viewers are subscribed - so please subscribe if you are interested in more videos!
What topics and level of difficulty would you like to see in future videos?
Until next time!
thank you for showing me why i have to learn the things in basic organic chemistry. i failed out over a year ago and have yet to return. you’ve inspired me to try again!
any chance of a cubane video? I find the 3D conformations fascinating and don’t quite understand how it happens fully.
Hi! I like your channel very much. I have actually been thinking of starting a similar one myself for a couple of years already, but I guess I was both too busy and too lazy to do so. To see such a kind of project put to life is very nice indeed! I subscribe and wish you good luck and successful development of the channel. The job you did is really appreciated!
Hardcore level please :)
Wow ur video's are amazing, the topic for the video's can be anything you find interesting. But if u want to optimalise views i would chose for more drug/explosive molecules. Personaly i realy like video's about current medicine. You can go as difficult as u want but I would recomend to Try to draw the steps as clear as possible to not scare away New viewers :))
The more complex the more interesting, but explaining the chemistry without being too lengthy will be difficult. I think this will help reveal the beauty of synthesis to people interested in chemistry. Not so much for casual science consumers.
And after a year, the Legend returned!
Just woke up and saw that you uploaded, immediately dropped everything and watched it.
Also hello /sci/bros.
Love this channel. Very rare to find organic synthesis videos for entertainment and not purely for academic presentation.
The UA-cam algorithm does bring to the surface some excellent content sometimes. This is one of those occasions. I have watched all your videos in the space of one day and I really do hope you continue to make more. Just hoping my grades are good enough to do chemistry at uni! Thank you for all your effort!
Very interesting video! I have tried Ginkgo Biloba supplements before, but didn’t notice an effect from them. It’s always good to know the chemistry behind what you’re putting in your body lol.
Thx for you awesome videos, the Ohtawa's and Shenvi's synthesis blew my mind a bit bc my org chem skills are nowhere near of those of an chemistry major and I’m a undergrad in pharmacy school rn.. I wish we had more of these org chemistry syntheses in our curriculum, bc sometimes it’s a little bit hard to understand everything (as I’ve forgotten already a bit :’( ), but your videos keep me motivated to teach myself everything so I can follow all steps :)
I find there’s something very interesting in each part of your video that lets me skip to google back and forth all the time haha
Keep up the good work pls! 🙏🧪👨🔬
You are exactly my target audience! Thanks for watching!
This channel is one of the most valuable ones I´ve ever seen!! I enjoy the quality and I need to say that I learn about a huge amount of reactions in the contents available here (which could certainly be of great use when i start to study). Keep going!!
Finally you’re back! Great work!
Dude! Missed your videos, great content as always. Keep synthesizing👌🏼
I've been telling people I couldn't find any channels like mine, yet here you are, doing it better. Cheers!
Incredibly cool and your color commentary actually bought out a sense of the elegance in many cases. I'm a normie but was able to follow along what what happening structurally by tracking the diagrams and parsing your narration. Thanks for a look into this world.
Great that you're back !
Its so great seeing this videos. I'm a total synthesis enthusiast.... Still have so much to learn from the background.
Great work glad you're back
really cool to see the evolution through the ages. so many cool reagents!
I always wish you would post more often. Amazing videos!
THE KING HAS RETURNED!
I would really love to see the total synthesis of vitamin B12 by Robert B. Woodward which allowed him to win the Nobel Prize in chemistry. He characterised the molecule by IR spectroscopy!
I'm so happy you are back
Thanks for your videos! They are so useful and very very interesting! Please do more!!!
Thank you for your amazing work!
amazing video, thank you
Huge compliments for your videos, its awesome and refreshing renewing memories of all thediverse reactions that organic chemistry has to offer. I know your channel is rather hardcore and maybe the possible audience is not huge, but please keep it coming. There is so many more interesing synthesis to be shown! Why not compare the biosynthesis with the artifical synthesis of some interesting compounds (maybe like Chloesterine or anything).
I personally would enjoy the videos to be even longer and more in-depth, with even more emphasis on the different name-reactions and background on how organic chemists cope with all the challanges in (total) synthesis.
great video. keep up the good work.
people might be interested in a video on the melatonin, serotonin, tryptamine realtionships and synthesis
Amazing work! Congrats
This is interesting, and is giving me ideas for a project in my lab...
I'm a master student and could not understand a lot of steps 😑. total synthesis is quite hard. thanx for uploading. looking forward to watch new interesting a bit detailed videos 😊
Awesome video, keep it up mate!
Finally u r back mate, keep it up 😊
Love that [2+2] addition to set up that clutch Bayer-Villager later. I got hyped when I saw that ketone installed, idk why, but I just love Bayer-Villagers, and [2+2]'s are probably my favorite cycloaddition.
I'll actually be taking my first real foray into organic synthesis this semester with my second research rotation for my PhD, and your videos have helped out a lot in making synthesis accessible, cause lord knows they try to bore you to death with their papers, lol.
(also, it's probably not really up your alley, but it'd be sick if you ever did a video on the use of biocatalysis in organic synthesis, cause that shit is my jam)
Super, good luck!
So happy you're back!!!
Excellent video! Subscribed.
BASED SHILLING ON 4CHAN
if the quality is high, it's allowed ;)
You should make a video about Chematica/Synthia software, which is THE REAL REVOLUTION. Also consider Nicolaou synthesis of Calicheamicin/Shishijimicin A, with their peculiar enediyne fragment. Great channel!!
Thank you......its awesome..
Awesome video. Bilobalide "made easy explanation"! For future videos I would like to see the evolution of total synthesis of Taxol with at least three examples showing the time diferences in state of the art of TotSyn of this historic molecule.
dang me too. also, i would like a series where you go into disconnection logic and how new methodologies enabled new logics.
something to do during lockdown!
I liked it. I think the history and people aspect was very interesting. The chemistry details were a bit dry but if part of the reason to do it this way is to teach yourself that’s fine. If you want to inspire perhaps you could simplify and include more how to details.
You could cover a polyketide like discodermolide, although there have been so many good approaches to that particular molecule. Lots of opportunity for stereoselective transformations!
I like your dedicated videos about organic chemistry & phytochemistry; is it possible for you to make a video about Endoperoxides? Or Sesquiterpene Lactones?
More more more !❤️
First. Nice work 😉👍
MVP
Hey, mate, I was wondering if you can do a video about bio compositions, which can increase life span? Prevent aging maybe?
Subscribing Normie reporting in
What about some Hanessian total syntheses? They are quite interesting too. Thanks
nice
I love the style of these videos.
On another note, do you watch Synthesis Workshop?
Thanks! I don't but have seen it pop up and featured it on my channel :-)
The Cyclo Edition is really good too.
Review - don't start with more complex compounds start compounds and reactions of 11,12th class or basic graduation level BS/B-PHARMA level with interactive so people develop interest in o-chem.
Beside doing great and helpful videos. great explanatory video
Well, although the organic synthesis sounds nice on paper, the efficient way to produce those kinds of compounds will always be the expression by GMO bacteria or plant monoculture like it was in the case of Taxol.
Do a video on dmt
4:09 why do you put the dots on the ginkolide molecule and not just specify the configuration?
are you possibly swiss german? I just discovered you and really like your videos.
Thanks! Yes I am :)
idk if i'd call swapping H2O2 to mCPBZ as luck, wasn't it a common reagent by then?
also 22:37 looks strange. in the molecule, the OBz is gamma to the ester while in the model you draw, it is only beta. am i missing something here?
also, my favorite part of the syntheses has got to be the stereoelectronic discrimination between various hydroxyls, epoxides, and alkenes. really great lessons to be learned, especially for the synth of highly oxidized polycycles. nice presentation
It was luck that it actually worked :)
What's strange exactly? OBz is gamma in both
Thanks!
in that case, i guess every synth is lucky
oh i see, you put the p orbital over the O, it makes sense. thanks for the helpful reply!
🤔 need advice in terms of reading material in the area of organic chemistry, specifically synthesis pathway design; so far I got McCurry - Organic Chemistry; and Boyd Morrison - Organic Chemistry; any advice is much appreciated.
Warren, Wyatt - Organic Synthesis: The Disconnection approach is good for retrosynthesis
For more basic org chemistry, Clayden’s book is great
Nicolaou’s Classic in Total Synthesis are case studies of complex syntheses - nice to read but not necessarily the most instructive book
How would synthesize 5 meo dmt?
sorry but can i ask a question?
at 07:26
why ozonolysis only cleaved one double bond?
Given the other alkene is tri-substituted, it reacts slower than the di-substituted alkene. The authors didn't comment on the detailed reaction setup in the papers - but if I would have to guess, they probably used an indicator to monitor the reaction.
These are dyes that also undergo ozonolysis (thereby changing color), but are chosen by the chemists so that they react slower than the first bond (that you want to ozonize) but faster than the second bond (that you don't want to ozonize). This way you can "stop before it's too late" :-)
Armin, is this you? The voice and the chemistry enthusiasm would fit... ;)
Indabox. Could be *very* useful for chemistry puns
Very useful for Total synthesist... Try to do more videos
I love you mister sintesis total please come back
🤣 will post another video surely this Summer during my vacation. All the best until then!
@@totalsynthesis awesome :D
9:32 that epoxide deoxygenation using Et3SiH at 300 degree~~~ reporting 90% yield... Is this the actual condition? Very typical late 1980s total synthesis paper.
ginkgo is the most based tree
If you show the actual synthesis and workup (wet lab) that is highly appreciated
What do you mean - experimental procedures?
Algorithm comment
holy sh*t. Last synthesis: Definition of "he who has absolutely no life". Insane chemists
😂
Do a complex natural product synthesis, except ditch the PowerPoint presentation and use a chalkboard, colored chalk, wear a suit and blue tie, smoke a cigarette and drink scotch. :oD
far out, the opposite of "normies get off my board"
Am normie