Organic Chemistry Walkthrough Steroid Total Synthesis: Equilenin, Retrosynthesis, Reaction Mechanism
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- Опубліковано 1 чер 2024
- In this video we will talk about the total synthesis of steroid hormones in the early 20th century. After an introduction into the history of steroids and challenges with steroid and natural product isolation, we will go through the retrosynthetic analysis .
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www.total-synthesis.com
Welcome to this channel around the topic of organic synthesis. This is not an experimental channel showcasing chemical experiments but rather will deal with theoretical discussions of syntheses of important chemicals and interesting natural products. If you are not familiar with organic chemistry, do not expect to understand everything I'm talking about. Please consult the literature, the myriad of youtube videos about basic chemistry or just Google.
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 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
Oh yea!! Finally!!!
I’ve been really interested for a long time in very long, multi step and complex complex synthesis of larger more complex biological compounds.
Also please go back to the animations you used to do that showed the mechanics of each reaction. I love the attack emoji with the bandit holding knives!! We need to see that guy, and all his friends in more videos.
Remember the true genius in any communication or education on complex matters, is being able to explain something in a simple way that anyone can understand, at the same time without dumbing it down to the point where information is lost.
Also I really wish that many synthesis were not so frowned upon here on UA-cam. The chemistry, retro synthesis and retrosynthetic analysis of of compounds like Lysergic acid diethylamide (for example) is utterly fascinating.
I feel as tho biosynthetic production processes will ultimately hurt the continued search for better synthesis techniques, and that’s kind of sad to me becuase I love reading about the hard work and dedication so many people contribute over many life times to the pursuit of getting rid of that one extra step, or some crazy out of the box idea that attacks a bunch of reactions from a completely novel way. It is the pursuit of novel and successful ideas in this very technical context that made me absolutely fall in love with organic chemistry in the first place.
These are the stories I’d love to see more of out in the world :)
Also oestrogen and it’s variants, as well as insulin. Absolute bangers for this kind of story telling and technical “MacGyvery”
Thanks for you comment and support!
Super interesting video, and I thoroughly enjoyed it! I’m Looking very forward to more videos :)
These videos are so great definitely keep it up !
Would have really appreciated seeing this during the early days of OChem.
Wish we could direct some more of the appropriate minds to your videos.
Excellent work and inspiring.
Perfect entertainment for autistic chemist like me
Love it
Again another great video - for the retrosnthetic analysis, it might be easier to understand if you show the disconnections and the corresponding synthons/synthetic equivalents. Just an idea
i think the disconnections might be helpful however, the synthons, retrons etc. are not
very nice and informative ... thank you much for your effort
Another one so quick?
take your time. eventually it'll be hard to keep up at this pace!
good work though.
Also, i feel this one is a bit rushed (as you said yourself). there's barely any time to digest what step just took place, and especially as an undergrad (4th semester), it's hard to keep up.
I potentially won't be able to upload in the next two weeks so I wanted to make another one. The synthesis employed pretty straight-forward reactions but I do agree that this one was very concise.
Thanks for following and for the comment!
I'm scared of watching most other videos of your channel, thinking I might get on some kind of anti-drug list.
sehr gut!
You're awesome, hope you Jeep going with the channel
I hope not. Jeeps don’t tend to keep on going, but this channel absolutely needs to!
Maybe it is too much to talk about yields on these videos but I would love to see maybe an image of the complete synthetic schemes drawn out with the corresponding yields in each step to supplement these videos. Overall, these are wonderful!
puresexcellence I will for more modern ones, yields in 1900-1950 syntheses are very rough and sometimes even omitted but youre right!
Still interested in those high caliber papers. Do you think you will get to them anytime soon? Do you potentially have a discord?
Hah, I forgot about this given it was recorded 5 yrs ago but I have since covered obviously some syntheses. The septedine one is however pretty nice so I might talk about it in a future chemistry-focused video. And at the moment I don't have a discord
Hi. I got intrigued, why the wavy curve after the Reformatsky reaction (at time 6:19)?
Miguel Goncalves The dehydration results in a mixture of (E) and (Z) alkenes
Didnt finish the steroid series🎉🎉🎉
I have one question about regioselectivity in one place, 6:35. Why only one got methylated?
Both got methylated but only the less hindered one got hydrolyzed again!
@@totalsynthesis In what conditions this may be performed? I don't like such messy steps to be sure... but they're kinda magic!
Hey brother you and I should sit down and brainstorm some polycyclic compounds to make broadly interesting videos about and then split them up between us. And then I need to sit down and put more effort into my own videos so you don't get frustrated by me doing a worse job on compound x than you would have done and now you have to make your own video to clean up my mess, lol!
isolating steroids from nature isn't entirely dead though. one of the ways that professional athletes get busted for exogenous testosterone is the ratio of carbon isotopes in their testosterone. plant derived testosterone has a different carbon isotope ratio to animal derived testosterone. apparently some top athletes have their testosterone extracted from animal sources
Oh wow thats interesting, thanks for sharing
How can I contact you...
Das DDR was good at steroid synthesis.
Start doing a backup or making a BitChute account ‘cuz YT doesn’t like chemistry, the place is full of retarded assholes and will eventually flag your vids or strike your channel, your content is so clean and well presented, it will be a shame to see this channel go, as many before you. Plan ahead share your twitter, patreon, reddit or whatever we can keep up with you beside this yt project. Good luck, this channel will do great!
Yes unfortunately I second this!!!
Are you a swiss gangsta?
Yes
You have some absolutely gigantic boots to fill. Some of the all time titans of organic chem have come out of this place. There must be something in the water 😂😂😂
i wish police would donate steroid precursors to me
😂
thanks gonna make tren now
😂