Advanced Organic Chemistry: Total Synthesis of Gibberelins, Retrosynthesis, Mechanisms
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- Опубликовано: 2 фев 2023
- Gibberelins play a critical role for plants and mankind being vital factors for plant growth and agriculture. They are the reason why we avoided a global hunger wave in the 20th century, and their analogs could open new mechanisms of action against cancer! This makes synthetic access and further biochemical and pharmacological studies even more important.
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01:27 Gibberelin's role in nature and agriculture
04:38 Isolation of natural products
06:54 Retrosynthetic analysis and strategy
09:02 Forward synthesis and mechanisms
Main paper: Concise Synthesis of (−)-GA18 Methyl Ester (Lei Li, Weida Liang, Mario E. Rivera, Ye-Cheng Wang, and Mingji Dai); doi.org/10.1021/jacs.2c12470
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) 
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Let's gooo another Episode!! 💥🥳
I am not even through my first semester yet. After watching this video I am very confused, maybe a little scared, but absolutely certain I choosed the right study.
Can always check the other vids to learn more 😎 stay at it!
The past tense of choose is chose, not choosed
Best Channel here at RUclips, even for professional organic chemists!
🥰
The use of a Lanthanide salt as catalyst not once but twice, makes this synthesis really funky.
On the topic of dwarfed plants: I grow Bonsai trees as a hobby. (They are not a species, but simply regular Trees that are grown to stay small.) Some species produce regular sized fruits, even when grown as bonsai. An example would be Lemon trees: I once saw a 20 cm tall lemon-bonsai with 4 fully sized Lemons. That's an an insane ratio of how much of that plants biomass is in the fruits. The effect on the root-system is also profound. As the roots are also developed by human intervention (for both the health of the tree and the
A e s t h e t i c s ) Bonsai trees will have a lot more fine feeder roots in their root-system, allowing them to get more nutrients ans water.
Which also results in more flowering and fruiting in some species like lemon trees for example.
Your videos are always amazing, keep being based.
Thanks man. Cool hobby! Oh wow, lemon bonsais lol
Neat molecule, very interesting use. But looks like a pain to actually synthesize in the lab.
fantastic work!
thanks man for these videos... state exams are coming and these synthesis are awesome examples of many of basic reactions put neatly to one video and I always stop to ponder how would I do that reaction
Thanks and good luck!!
GA3 is cheap, but many times quite useless for induction of flowering and so I needed GA7 (not sure I recall that correctly). But I rejected the option quickly when I saw the price!
So, yes, we need good ways to synthesize gibberelins.
6:57 Mario Rivera- I know that guy
Hi Hunter
don't forget plant ecologists!
On those low yields from large scale raw materials- percent yield may not apply here but plant hormones like all hormones in living systems: a little goes a long way.
Is this Anton?
I am hoping so. ✌️
"6-4-3 tricyclo bridged carbon" should not be in the same sentence with "nice to look at". Practicing and being fond of witchcraft is an offense worthy of being burned at the stake.
Also really sick vids. I really enjoy it and both of your editing and presentation have gone better and better. Its entertaining and really tingle your brains to start thinking.
Your community page is also fun. Imo top 5 chemtuber material easy
Lmao. Thanks!! Means a lot!
Great video, intelligent. But advancements in food production just help until people populate their way beyond them. Then, usually we are worse off than without development. If I needed this, I'd study the mechanism of it's effectiveness first, if possible. And then create something simpler that has the same effect. Though, I can see that one may need to synthesize the molecule of interest first to have enough quantity to study it.
So why NaBH4 did not reduce that ketone? Thx
The aldehyde is more electrophilic and reactive, so by using just one equivalent of NaBH4, the ketone is not reduced in significant quantities!
@@totalsynthesis thanks! That makes sense.
so many people are fed with the help of synthetic fertilizers ... the way they are excluded out of food production nowadays worldwide, would imply that many many will die of hunger pretty soon .
Say what 😭