How one of Nature's Most Complex Molecules Is Made: Synthesis of Taxol's "Complicated Cousin"
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- Опубліковано 10 чер 2024
- Taxol - a commonly used anticancer drug - is part of a broader family of taxane natural products - which includes Canaxpropellane, Taxol's "complicated cousin". We will explore some of the related - and unrelated :) - history, biochemistry and chemistry facts and trivia.
Even if you are not deeply engaged with total synthesis, I am confident that this video will enrich your understanding of natural sciences.
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00:00 Introduction
00:32 Setting the scene for Canataxpropellane
03:48 Propellane nature, reactivity, utility (bicyclopentanes), history (Ginsberg)
07:55 Simple synthesis of [4.4.2] propellane
10:08 Total synthesis of Canataxpropellane by Professor Gaich and co-workers from the University of Konstanz (retrosynthetic analysis, disconnections, forward synthesis, mechanistic disussions, stereoselectivity)
19:59 Summary
As always, let me know your thoughts on this video and ideas for future ones. Please take a look at my other videos if you are interested and subscribe to the channel if you would like to see more!
Key references:
- science.sciencemag.org/conten...
- pubs.acs.org/doi/pdf/10.1021/...
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
This video makes me realise I need to go over my year 1 undergrad chemistry notes again
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Fantastic, what a brilliant synthesis. The BHT serendipity was great. Thanks !
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When this channel uploads, I have a good day
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based molecules
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Are you on the "that chemist" discord or something?
@@richardlyman2961 that will do it... anything drug related could get you in trouble too...
Great video! One note--the molecule at 5:13 was developed by BMS, not Pfizer. I know because I was on the team that made hundreds of kg of it. My first project in industry and a fun project as well.
Thanks for clarifying. Of course you’re right, the original inhibitor was BMS and just the BCP analog was Pfizer.
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🤯
So stunning.
I'm not organic folk, though. yet it's really interesting to watch.
Keep your great work.
Thanks!
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this videos are awesome !! keep doing this fantastic job!
Hi, perhaps you will like my channel about recent chemistry publications. Just released a video about the recent work of Benjamin List (the guy with the 2021 Nobel prize) ua-cam.com/users/ChemNewsvideos
Great synthesis and great video. Amazing!
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I'm an undergraduate chemistry student at a university in Taiwan, and UA-cam has finally recommended to me the video I really want to watch, instead of random/clickbaiting videos.
12:00 Is where I start to have 0% understanding lol.
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maybe you should consult the paper. it is greatly written and perfectly understandable with a little knowledge of organic chemistry
Very well done! Congrats on putting together a really great video on this complex target!
Thank you! Great work on your videos as well, I featured you on my channel page if that helps in any way :-)
Hi, perhaps you will like my channel about recent chemistry publications. Just released a video about the recent work of Benjamin List (the guy with the 2021 Nobel prize) ua-cam.com/users/ChemNewsvideos
a beautiful synthesis. Pericylic mechanisms are so powerful in the construction of these stereogenic centres. Appreciate the detail and care in presentation.
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Your videos are brilliant, I really hope you will post more often in the future
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It came different!!! Awesome update to ur request on Taxol, excellent surprise!!
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A very nice video indeed, thank you for making them!
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crazy synthesis 💯
Great to know what was the initial thought process of total synthesis of these complex molecules..Thank u so much for providing this informative content..
Lots of Love From INDIA 🤩🤩
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Very nice video, glad you highlighted this one as I was not aware of this science publication of her
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I have just read this original literature in July. Very impressvie for this total synthesis. When I was reading, I followed this literature and drew every steps in this synthesis. Art of total synthesis
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I love your channel. You are a master.
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Just fantastic!
My PhD is on this complex molecule,Taxol.. Nice to be a part of its synthetic studies...
Nice, good luck!!
Need more videos like that.
I vote for video with explaining of carborane acid synthesis ^_^
I love your unique topics and approach to organic sinthesys, you might not be able to upload often but quality never drops,keep it up!!
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love the vids man
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Another great video
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Fantastic!
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Thank you so much for your work! You are awesome.
Hi, perhaps you will like my channel about recent chemistry publications. Just released a video about the recent work of Benjamin List (the guy with the 2021 Nobel prize) ua-cam.com/users/ChemNewsvideos
@@ChemNews With great pleasure! Thank you.
@@crabcrab2024 Thanks!
Great video once again! Keep up the good work :)
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nice video
Great video
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Hi!
I'm graduating my B. Sc in chemistry, and i'm currently doing a chemistry methods course.
We learn how to synthesise polyfunctionnal complex molecules. We had to explain the uses of all the protecting groups in litterature.
Your videos really helped me to understand why using MOM chloride in certain cases instead of Boc.
Your videos help (probably) lots of people, and we are super greatful of having your help!
Keep it up :)
Very happy to hear this! Wishing you all the best for your courses :)
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Danke für das interessante video!
In der Tonaufnahme ist viel Hall, vllt kann man das günstig mit Isolation an der Wand verbessern (Schaumstoff, Eierkarton; klingt wie ein kleiner Raum bzw. direkt vor einer Wand aufgenommen)
Awesome👏
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Why this Chanel not putting videos anymore, very interesting stuff
Total Synthesis:
-Covers decades of org Chem history, about a group of Molecules only known by
people who actually studied/ worked in chem and total nerds.
-Introduces the audience to a absolute Raid Boss of a molecule (in terms of complexity)
-Covers the development, retrosynthetic considerations and most of the 26 step total synthesis.
And he did all of that with in a little over 20 minutes and with a calming voice.
Beyond Based.
PS: I was really surprised how how stable that Peroxide was. That Synthesis was a wild ride.
Love you!
Hi, perhaps you will like my channel about recent chemistry publications. Just released a video about the recent work of Benjamin List (the guy with the 2021 Nobel prize) ua-cam.com/users/ChemNewsvideos
Thank you for sharing! Just searched for Taxol Synthesis as I got news today that I'm gonna do my bachelor in the AG of Prof. Gaich. Really exciting.
Amazing. All the best!
@@totalsynthesis I've got some questions concerning the use of the building blocks (dienophiele and diene). Would it be possible to get some more insight into the mechanism of the [2+2] cycloaddition as well as the reasons for choosing these two substrates? Sure, regio- and diastereoselektivity are key to achieving the endo-diels alder adduct, but i would like to know some more detail. Since you put all this effort into this video, maybe you want to pass some of your findings to me?
regards
thanks
Brilliant.
Hi, perhaps you will like my channel about recent chemistry publications. Just released a video about the recent work of Benjamin List (the guy with the 2021 Nobel prize) hua-cam.com/video/ELy3uR9Bsm4/v-deo.html
I can't follow you longer than some seconds because I have no clue of the topic but I like to listen to your beautifully calming voice ❤️
Hi, perhaps you will like my channel about recent chemistry publications. Just released a video about the recent work of Benjamin List (the guy with the 2021 Nobel prize) ua-cam.com/users/ChemNewsvideos
really nice vid!!
Hi, perhaps you will like my channel about recent chemistry publications. Just released a video about the recent work of Benjamin List (the guy with the 2021 Nobel prize) hua-cam.com/video/ELy3uR9Bsm4/v-deo.html
@@ChemNews lol okay I'll check that out in a bit
@@ChemNews also I suggest I not comment on everyone's comment or UA-cam might think u r spamming
@@NightLightnight If you change the text a little bit - youtube does not mind :)
Unfortunately, there are not too many ways to get new subscribers in the initial stages of the channel...
Fantastic video!!!
Hi, perhaps you will like my channel about recent chemistry publications. Just released a video about the recent work of Benjamin List (the guy with the 2021 Nobel prize) hua-cam.com/video/ELy3uR9Bsm4/v-deo.html
you uploaded this in the middle of an LSD trip this is NOT a coincidence what
WHAT
nightmare nightmare nightmare
good travels!
here's a video if you need to CALM down (click on the link): ua-cam.com/video/HFacq4vKMw8/v-deo.html
oh and btw it was an excelent video and very beautiful experience believe it or not, for some reason his voice has this smile inducing undertone, very charming
the reactions were fascinating as well, very good experience overall
@@lucidchem thankfully i didnt need your video, but thank you!
@@knivesnico8775 No worries, I'm glad to hear that!
Could you some day talk about the total synthesis of gingerol (chemical present in ginger)?
yes, gingerol is immensely important
wow, the dearomatization cycloaddition is really nice!
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whats the thing at the beginning that says not this maybe later?
Absolut madlads
Niduterpenoid A seems very complicated molecule as well, do you think we will see soon it’s total synthesis? Congratulations for your Chanel, this kind of contents are not so common in youtube
Definitely looks interesting!
Thank you!!
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Please make video about ONC (octanitrocubane) synthesis
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Actually got to watch Tanja Gaich give a talk on this. My mouth was in the floor for 30 straight minutes
Cool!
Based synthesis
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How do you explain the regioselectivity reduction of the ester in presence of a ketone using LAH ? In my understanding LAH should reduce a ketone very easily 17:50 min
I think it’s just sterics - even though “the bottom” face looks open, the attack trajectory of nucleophiles would be quite shielded by the bulky acetal group. So the ester gets reduced first. The authors didn’t comment on this - but I wouldn’t be surprised if they saw some reduction, especially at more forcing conditions
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Hello!
Very interesting video. Tell me, you can meet a trotofan bromination reaction or tripartamine bromom in a 5th position. And then in the Russian-speaking literature such a technique to find a gentle. I really know English very badly and I find it difficult to search for such a technique.
Do you have access to reaxys? This database shows different ways to prepare chemicals
Are you talking about direct 5-bromination of tryptophan? Not sure if that is possible, you probably need multiple reactions via the 5 bromoindole or others
@@totalsynthesis I'm from Ukraine. I am a little difficult to speak English.
I do not have access to REAXYS. Give a reference to Reaxys. For me, very interesting foreign works of chemists. Maybe I find something for myself.
8:45 would this not be 1,3-butadiene?
Yep, misspoke
Thanks for that, very clear. However, I expect it will be more complicated on a second viewing!
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So did it cure cancer? I think this would be pertinent info.
No but it looks cute
If I had a penny for each word I didn't understand, I'd be able to open copper foundry.
Here's a penny for watching the video regardless 🪙
@@totalsynthesis what class. & anyone who says "melting pennies is illegal" is just volunteering to be your lab assistant/slaves.
more videos plz
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@@ChemNews thank u so much for you work, i apreciate it .
This is why I did bad in orgo. Just seeing synthesis after synthesis frustrated me because I need to understand why each step behaves the way it does and they all have some crazy explanation I'm always either skeptical of or don't understand. And then on the tests all my synthesis proposals are wrong. Each step could take hours to days, and your yield is going to be tiny. 26 steps must have taken months.
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by Gaich Group.
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Am I a bad viewer for using your video to cope with my insomnia? 😂😂😂
No, glad I can help ☺️
I can make a pitcher of kool aid all by myself.
Teach me your ways
here's a comment for the algo
💪
Penguinone
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