This is what peak Organic Chemistry looks like | Retrosynthesis & Modern Total Synthesis
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- Опубліковано 10 чер 2024
- In this video we cover an amazing natural product total synthesis - peak organic chemistry.
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If you have some organic chemistry knowledge, you will enjoy this video as we review history and natural product isolation, retrosynthetic planning, chemical synthesis and structural elucidation of a harziane diterpenoid natural product. If you're less knowledgeable, this video will show you how modern organic reactions are applied to total synthesis of complex molecules.
Correction to 11:00: Diazo group (N2=) on the Ohira-Bestmann reagent
Total synthesis and structural revision of a harziane diterpenoid (Hönig, Carreira): onlinelibrary.wiley.com/doi/a...
chemrxiv.org/articles/Total_S...
Isolation reports:
2014: www.sciencedirect.com/science...
"2020": www.sciencedirect.com/science...
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
9:11 is there a reason to suppose, that the cyclometalation proceeds with Pd(II) and not with Pd(0)?
That particular reaction is Pd(II) catalyzed, not Pd(0) - JACS 1985, 107, 1781 ("A Pd(0) species such as (Ph3P)4Pd does not catalyze reaction after 12h at reflux in THF")
Related references on mechanism: JACS 1994, 116, 4255 | Acc. Chem. Res 1990, 23, 34
There are however probably similar, Pd(0)-catalyzed reactions with different conditions/ substrates (had a quick look, e.g. JOC 2004, 69, 6697)
@@totalsynthesis Thank you for your reply! Keep on making amazing content!
Mr. Woodward, you were supposed to know that!
@@jozsefszaszi355 Dear sir, me and prof. Eschenmoser are only starting to get into this novel palladium catalysis.
@Jm Cresencio that would then mean that Pd(0) is catalysing the reaction, which is the purpose of the use of Pd(OAc)2. the acetate ligands are supposed to be quite labile so they come off quite easily, allowing catalytic pathways to initiate requiring the non-complexed Pd(0). a Heck reaction is one such example of this catalytic pathway being used in synthetic application.
I clicked this knowing I wouldn’t understand a thing.. I indeed didn’t understand a single thing, but it was fun to see all those hexagons saying “Me.”
xd
It's started off good then I completely got lost 😂 I guess I'll have to do more research on synthesis before this will make since to me
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me who failed chemistry 3 times: i like your funny words magic man
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I AM SO HAPPY I FOUND THIS ACCOUNT. As a chemist in the drug Feild I am blow away at this synthesis. I complain at a 6 step synthesis...kudos to these nerds
Can you help me with a methoxetamine short cut? I need to get around the microwave proton rearrangement I don't have the apparatus
Stop poisoning people and give them vegetables.
nature put medicine in the food
@@obviouslytwo4u Ah yes, eating veggies will help you with TB. Truer words have never been spoken!
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Fantastic! I thoroughly enjoyed the perspective of newer total synthesis. The guys who do total syntheses these days are way past super saiyan.
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This is great! The only problem I can see is there's not enough content!
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commenting for algorithm reasons!! these videos are awesome, and im in awe at your ability to digest big papers down into an engaging format! keep it up!
One of the most genius underrated channel on UA-cam....keep going on brother
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Thank you for your videos, they are very interesting for an undergrad like me interested in total synthesis and retrosynthesis.
Keep up with the good work.
From Italy.
Hello, GREAT material with a perfectly paced delivery. Please make more videos, these are so informative and make the material much more understandable/accessible. Thank you for your patient and thoughtful insights to the chemical world!
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Great video, I am waiting for more!! Take your time of course, is not easy to summarize a total synthesis and the target audience is very limited, but I am sure that if u keep publishing this kind of videos, all the community of synthetic organic chemist will know about you!
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so beautiful!! finally a youtube channel that really gets into the chemistry
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Absolutely mind blowing synthesis. Very nice video, keep up the great work!
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I feel very grateful to have found your channel
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Wow! Very cool! Love to see a total synthesis video on youtube, and one that is very well done! Hope to see many more like this in the future!
Thanks! More in the works ;)
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These videos are great. I wish there would me more of them! I appreaciate doing neat and nice ChemDraws such as the ones you show take time, but it is worth the effort! I would certainly spread the news of this videos to other chemists I know would enjoy!
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Coming back to this after following an organic synthesis course is very satisfying
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I wanna thank the UA-cam algorithm for suggesting this to me. This is the first video I saw and its the one that made me a subscriber. as a second year chemistry student myself, I am proud to say that I understood most of what was going on.
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Nice video. I enjoyed learning the history as well as the organic synthesis. Subscribed-Keep up the good work!
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Thank you for this effort!
To say well done is truly an understatement.
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Great video! I'm glad I found your channel, I'm sure I will learn a lot. It's hard to memorise everything from such a blast of information but if you memorise one thing for each video, you will slowly be a better chemist.
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Great video, thanks for putting it together. Was nice to be able to recognise a lot of the transformations from my organic lectures! Modern day wizards, these guys.
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Your content is great !Please keep on posting !
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So glad to see a channel dedicated to recent multistep syntheses. Perfectly narrated, tho had to look up half of the name reactions
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Great job! Thank you so much
Keep doing this videos! Best of UA-cam!
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this kind of "casual" org. synth. is exactly what i needed. thanks.
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Please keep making videos if you can, I know UA-cam and life in general don't reward content like this much but what you do is important to get the small group of interested people to dive into this subject and potentially go on to make important discoveries.
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Outstanding. Will be coming back when more content is posted.
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I've found ur channel on /sci/ months ago, had it bookmarked since then now that i got this vid recced i v become really intrigued to learn chemistry, i underwent chemotherapy and used taxol so this definitely relates to me, really appreciate the video hope to see more of
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Superb Total synthesis video. I was very excited by seeing this video. Total synthesis is good approach for applying, practicing organic reactions and retrosynthesis. Please upload more videos.
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Awesome video, thanks!
Glad you liked it!
So helpful. This has almost every reaction from my Total Organic Synthesis class. It's like a condensed version of the Modern Organic Synthesis book by Somfai. Thank you so Much. Really interesting synthesis.
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please we need more videos like this!
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Recently i studied for special methodologies in organic chemistry and i was pretty amazed when you spoke about the taxol and the background, then you procedeed to explain the synthesis...
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Хорошее видео. Спасибо за работу, комрад)
Amazing video! Immediately subscribed.
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holy shit man, these are some mad organic skills. great video!
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OMG this Channel is amazing how are u still so relatively small Great work keep it up!!
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I cannot understand antything but somehow it seems super interesting. Like puzzels for really intelligent people. I loved chemistry back in middle school. Shame that I lost it in the high school. It still fascinates me and I wish I could understand it.
Thanks for watching nevertheless haha
Very nice Video! I even recognized some of the more "easy" steps such as the Wittig-Reaction or Ozonolysis.
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Incredible videos man!
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Currently working on my seminar presentation on the Baran lab's Taxol total synthesis route published mid 2020. It was cool watching this vid and being familiar with all of this stuff.
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Very well made video! I am glad i don't do total synthesis but it is super interesting to learn about
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amazing amount of information
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hey i love your videos man and i would wish for some more deeper mechanisms
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Awesome! You really need more views!
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This is challenging and interesting. Hope to see more. I didn't multiply the % yields but am guessing they needed a lot to start...great video.
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Excellent video, thanks! :)
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Being a synthetic chemist researcher it is quite interesting and inspiring to continue work I know that it is not easy as it seems on paper......it takes years to design such a complex synthesis
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Since this video took you a sheetload of time to think about and make, I will honour you with a comment.
You're welcome!
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Excited to see this
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I'm a Bio major but I have absolutely fallen in love with Organic Chemistry; so much that I'm now a Supplemental Instructor for Orgo 2. It's just so cool!
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amazing video keep it up.
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This retro-synthesis is just insane.
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Great my friend!
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I LOVE your videos!!! Thank you for the content. Have you considered a different mic or audio balancing software? I’m getting a very low volume when I wtatch
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Carreira is an absolute beast. I'm new to the channel and I love every bit of it
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that's so beautiful
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Great upload thanks 😊
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13:50 haha that's the funniest way I've ever seen a hydration performed xD The water free hydration is brilliant.
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Very interesting content. You can rarely find anything about OC in UA-cam.
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THANK YOU.
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Please make more in depth videos like this
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This is amazing
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Nice review man - tiny typo with the Bestmann reagent - there's a diazo group missing.
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Absolutely great video, would love to skype you and discuss some natural products and chemistry behind them. I love learning from these videos! thanks
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Materials Chemist here...my mind is entirely blown apart by the retrosynthetic routes and synthesis. Holyyy.
How did you guys get good at this?
Many interesting possibilities in terms of reactions and approaches... and even more ways to "fail", leading to quite unique routes being explored
Thanks for watching!
What a clear and lucid presentation of such a beautiful synthesis. Amazing work (both Carriera and this channel!)
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I'd really appreciate if you discussed how advances in machine learning are contributing to advances in chemistry with specific regard to reaction prediction, synthesis analysis, pathway design etc
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Through out the synthesis, bestbpart is, before disconnection, hypothetical functional group introduction -OH group like acid group on cubane and removal at end. Here did in two steps, thieves formation then treated with tin reagent. Might be can use novel methods, like triethylsilyl hydride to get product in one step to remove -OH group. Overall good lecture and I requesting you provide more and more vedios like this. Thank you.
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Really excellent channel. I'm quite new here, but I look forward to delving more into the channel.
I'm curious, where do you get information on things like the total sale of drugs like Taxol? I see this sort of information in papers occasionally, as a way to motivate interest in a particular compound, but I never really know where to begin looking for financial information on pharmaceutical agents that I myself am making. I hope you see this, thanks!
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Nice presentation! But I couldnt help but notice some mistakes. At 13:17 methyl triphenylphosphonium bromide is displayed wrong and at 14:45 there is a pentavalent carbon shown in an explanation of the NOE spectrum.
what does that mean
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Nice video,. I have one question though,, why the protected methylketone that is leading the hydroboration is pointed with dash, is a racemic micture?
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I'm trying to synthesize methoxetamine without the microwave proton rearrangement step. Any ideas?
Danke .
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Great videos! I have one request, though, to make things a bit more easy to follow. Could you use a 'laser pointer' of sorts, to guide us through the molecules as you discuss them? It's sometimes kind of difficult to know which part of the molecule you're talking about, and to follow what you're saying at the same time. Especially with these complex syntheses.
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at 11.05 min, Ohira-bestmann reagent, N2 is missing!!!
What is the reason for the epimerization after treatment with the Ohira-Bestmann reagent? AFAIK, the Ohira-Bestmann reagent usually does not cause alpha epimerization, and I can't find an explanation in the paper.
Edit: I think it is due to base catalyzed alpha epimerization of the aldehyde via keto-enol tautomerism. The potassium carbonate base used with the Ohira-Bestmann reagent is able to induce keto-enol tautomerism on the aldehyde, which leads to conversion to the less sterically strained epimer.
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At 13:17. Is it possible that the reagent used in the Wittig-reaction should be Ph3P(+)-CH3? Otherwise, where does the Br go? In the conditions given in the publicaiton there is Ph3PCH3Br written, probably with a missing comma between the reagents Ph3P and CH3Br.
Youre right, I just copied that over without activating my brain
Hey,
I like your approach towards each video.
here's a small detail that I would like to add according to my opinion.
It would be more engaging if you add some background music.
thank you very much.
keep up the good work. (y)
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Was literally my favorite subject in graduate school. Fuck yeah.
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HATs off for mHAT hydrofunctionalization.
I really enjoyed the retrosynthetic analysis in this video, you do a nice job addressing the issues of complexity vs accessibility in a sparsely functionalized target.
Eccezionale la sintesi del cubano! Ma se facciamo una nitrazione spinta, cosa otteniamo? Complimenti
Grazie
Great video! But there is a small error. 10:58 The structure of Ohira-Bestmann reagent is incorrect. it's a diazo group at the bottom.
Thanks! Yep, I think I noted this in the description or somewhere after I realized 😇
Plz upload sandal oil retrosynthesis
Ohira-Bestmann is a diazo carbonyl reagent.
How did the team manage to protect only the one of the two OH groups in the step with PivCl? Is this reaction selective or more favourable kinetic product at lower temperatures?
Yes, it's selective as the primary alcohol is more reactive than the secondary!
Brilliant
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The thug glasses on E.Carreira cracked me up. Will try not to laugh when I see him in the hallway. Great video!
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Listen at 1,5 times the speed and it is much more listenable :D
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More of these please
Also they should have found the gene fir this bs and over expressed it in yeast ir something
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Do you think snow is water or snow is water + CO2?
Can you discuss some of the work by prof .Phill Baran
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One of my cohorts in my Graduate Organic synthesis class had to give a presentation on this molecule. He didn’t look like he enjoyed making the presentation though
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Lmao, poor guy
what is the overall yield?
11:03 is this the correct structure of the Ohira-Bestmann reagent?
Nah I messed up mate
Nice video and what a beautiful synthetic approach! I have only a point of criticism: you're too fast, at least for me. I would have liked more time to look at the structures before you removed them. I know that there is a pause button, but often I had to rewind a few seconds before pausing because you have already removed them.
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Sir, Is there a way to request a specific topic? I am an amateur perfumer/fragrance enthusiast and would like to be able to request a topic. If you have a Patreon account I would not hesitate to donate. Thank you, Tcheuss!
Hey Brent - fire away. Can't promise but what would you like to hear about?
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4:45 It's actually not the same depicted molecule. As you rightfully said it's a diastereoisomere... 😉 Greetings from another chemist. 😉 GREAT video though!
I have not worked as a chemist since I left uni 10 years ago. 😂
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