Simplifying Synthesis
Simplifying Synthesis
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Total Synthesis of Ganoapplanin
An organic chemistry minilecture on the 'Total Synthesis of Ganoapplanin Enabled by a Radical Addition/ Aldol Reaction Cascade' by Nicolas Müller, Ondřej Kováč, Alexander Rode, Daniel Atzl, and Thomas Magauer*. It features a stereoselective titanium promoted cyclization, radical cyclization-aldol addition and a bis-spiroketalization cascade.
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NMR Spectroscopy in music:
J. New Music Res. 2021, 50:5, 487-501
Socials:
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References:
J. Am. Chem. Soc. 2024, 146, 22937−22942 (This work)
J. Org. Chem. 1996, 61, 23, 8256-8263 (Cyclization)
Tetrahedron Lett. 1994, 35 (7), 1059−1062 (Cyclization)
J. Am. Chem. Soc. 1989,111, 6, 2204-2210 (Cyclization)
J. Am. Chem. Soc. 1965, 87, 24, 5684-5692 (Mesylation mechanism)
J. Chem. Soc. B, 1971, 182-185 (Triethylborane radical activation)
J. Am. Chem. Soc. 2016, 138, 24, 7741-7752 (Triethylborane radical activation)
Synlett 2017, 28 (13), 1576−1580 (Benzylic Oxidation)
ACS Catal. 2016, 6, 5, 3253-3261 (studies on electron transfer/hydrogen atom transfer mechanisms in CuBr/tBuOOH oxidations)
Переглядів: 911

Відео

Total Synthesis of Hypersampsone M
Переглядів 1,6 тис.3 місяці тому
An organic chemistry minilecture on the 'Total Synthesis of Hypersampsone M' by Adrian E. Samkian, Scott C. Virgil,* and Brian M. Stoltz*. It features an innovative ring expansion rearrangement, zincate addition-annulation and an aldol cyclization-lactonization sequence. SUPPORT THE CHANNEL ON PATREON: www.patreon.com/SimplifyingSynthesis NMR Spectroscopy in music: J. New Music Res. 2021, 50:5,...
Total Synthesis of (−)-Bipolarolide D
Переглядів 1,5 тис.4 місяці тому
An organic chemistry minilecture on the 'Concise Total Synthesis of (−)-Bipolarolide D' by Shengling Sun, Qi Wei, Yufei Liu, and Zhaohong Lu*. It features a highly effective [6 6] cycloaddition, a ring closing Heck Coupling and a Babler -Dauben Oxidation. SUPPORT THE CHANNEL ON PATREON: www.patreon.com/SimplifyingSynthesis NMR Spectroscopy in music: J. New Music Res. 2021, 50:5, 487-501 Socials...
Total Synthesis of Hunterine A
Переглядів 2,4 тис.6 місяців тому
An organic chemistry minilecture on the 'Enantioselective Total Synthesis of (−)-Hunterine A Enabled by a Desymmetrization/Rearrangement Strategy' by Elliot F. Hicks, Kengo Inoue, and Brian M. Stoltz*. It features an asymmetric Noyori Transfer Hydrogenation, an Aza-Cope Mannich reaction cascade and a creative triazoline photodecomposition. SUPPORT THE CHANNEL ON PATREON: www.patreon.com/Simplif...
Total Synthesis of Dragocins A−C through Electrochemical Cyclization
Переглядів 2 тис.7 місяців тому
An organic chemistry minilecture on the 'Total Synthesis of Dragocins A−C through Electrochemical Cyclization' by Brendyn P. Smith, Nathanyal J. Truax, Alexandros S. Pollatos, Michael Meanwell, Pranali Bedekar, Alberto F. Garrido-Castro, Phil S. Baran* It features an Electrochemical Oxidative Cyclization, an Barton-McCombie Chlorination and a divergent Moc carbamate reduction. SUPPORT THE CHANN...
Total Synthesis of the Allenic Macrolide (+)-Archangiumide
Переглядів 1,9 тис.8 місяців тому
An organic chemistry minilecture on the 'Total Synthesis of the Allenic Macrolide ( )-Archangiumide' by Jack L. Sutro and Alois Fürstner*. It features a Julia-Kocienski olefination, a ring closing alkyne metathesis and a conformationally controlled stereoselective 1-5 hydride shift to enact an alkyne to allene rearrangement. SUPPORT THE CHANNEL ON PATREON: www.patreon.com/SimplifyingSynthesis ...
Novel Psilocin Prodrugs for Treatment-Resistant Anxiety Disorders
Переглядів 1,1 тис.9 місяців тому
A medchem minilecture on the 'Novel Psilocin Prodrugs with Altered Pharmacological Properties as Candidate Therapies for Treatment-Resistant Anxiety Disorders' by S. A. Raithatha, J. M. Hagel, K. Matinkhoo, L. Yu, D. Press, S. G. Cook, G. Sharma, D. Dhananjaya, G. Jensen, J. B. Lee, C. Cai, J. Gallant, J. Bains, J. E. Tucker, and P. J. Facchini*. It explains the metabolism of psilocybin, how th...
Total Synthesis of (−)-Caulamidine A
Переглядів 1,7 тис.11 місяців тому
An organic chemistry minilecture on the 'Enantioselective Total Synthesis of (−)-Caulamidine A' by Zhouyang Zhu and Thomas J. Maimone* It features an asymmetric prenylation, doubled displacement annulation and adiastereoselective Hydrogen Atom Transfer reaction. SUPPORT THE CHANNEL ON PATREON: www.patreon.com/SimplifyingSynthesis NMR Spectroscopy in music: J. New Music Res. 2021, 50:5, 487-501 ...
Total Synthesis of Lissodendoric Acid A
Переглядів 1,6 тис.Рік тому
An organic chemistry minilecture on the 'Total Synthesis of Lissodendoric Acid A Via Stereospecific Trapping of a Strained Cyclic Allene' by Francesca M. Ippoliti, Nathan J. Adamson, Laura G. Wonilowicz, Daniel J. Nasrallah, Evan R. Darzi, Joyann S. Donaldson, Neil K. Garg*. It features a remarkably selective allene cycloaddition to build the azadecalin core, allowing for a ring closing metathe...
Enantioselective Synthesis of Nabscessin C
Переглядів 1,3 тис.Рік тому
An organic chemistry minilecture on the 'Enantioselective Synthesis of Nabscessin C' by Chun-Wei Yeh, Chia-Chi Feng, Pei-Lin Chen, Yi-Jhen Jhou, and Duen-Ren Hou*. It is a masterclass on using conformational and steric effects to selectively manipulate hydroxyl groups and features a highly effective enzymatic desymmetrisation. SUPPORT THE CHANNEL ON PATREON: www.patreon.com/SimplifyingSynthesis...
Convergent Total Synthesis of Cyclopamine
Переглядів 2,2 тис.Рік тому
An organic chemistry minilecture on the 'Convergent Total Synthesis of (-)-Cyclopamine' by Manolis Sofiadis, Dongmin Xu, Anthony J. Rodriguez, Benedikt Nissl, Sebastian Clementson, Nadia Nasser Petersen and Phil S. Baran* Highlights include an Asymmetric Allylic Alkylation, a radical Halocyclisation and a challenging Ring Closing Metathesis to form a tetrasubstituted olefin. SUPPORT THE CHANNEL...
Gram-Scale Total Synthesis of (±)-Ibogamine
Переглядів 2,3 тис.Рік тому
To try everything Brilliant has to offer-free-for a full 30 days, visit brilliant.org/SimplifyingSynthesis/. The first 200 of you will get 20% off Brilliant’s annual premium subscription. An organic chemistry minilecture on the 'Gram-Scale Total Synthesis of (±)-Ibogamine' by Alexander J. Hughes and Steven D. Townsend*. It showcases a highly effective synthesis featuring a Stork-Danheiser Trans...
Total Synthesis of (±)-Agelastatin A
Переглядів 1,7 тис.Рік тому
An organic chemistry minilecture on the 'Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A' by Rafael F. A. Gomes,* João R. Vale, Juliana G. Pereira, and Carlos A. M. Afonso*. It features a highly effective use of a Stenhouse salt to establish two the stereocentres that control the stereoselectivity for the rest of the synthesis. SUPPORT THE CHANNE...
Total Syntheses of Malettinins C and E
Переглядів 1,8 тис.Рік тому
To try everything Brilliant has to offer-free-for a full 30 days, visit brilliant.org/SimplifyingSynthesis/ . The first 200 of you will get 20% off Brilliant’s annual premium subscription. An organic chemistry minilecture on the 'Total Syntheses of Malettinins C and E' by Nariyoshi Umekubo and Satoshi Yokoshima*. It features an organocatalyzed aldol addition, an oxidative cyclization to form th...
Total Synthesis of Ineleganolide
Переглядів 2 тис.Рік тому
To try everything Brilliant has to offer-free-for a full 30 days, visit brilliant.org/SimplifyingSynthesis . The first 200 of you will get 20% off Brilliant’s annual premium subscription. An organic chemistry minilecture on 'A Convergent Total Synthesis of ( )-Ineleganolide' by Benjamin M. Gross, Seo-Jung Han, Scott C. Virgil, and Brian M. Stoltz*. The synthesis is the culmination of over two d...
Stereoselective Synthesis of (-)-Eugenial C
Переглядів 1,8 тис.Рік тому
Stereoselective Synthesis of (-)-Eugenial C
Prodrug Strategies Against the Varicella Zoster Virus
Переглядів 760Рік тому
Prodrug Strategies Against the Varicella Zoster Virus
Total Synthesis of Cephalosporolide F
Переглядів 2,1 тис.Рік тому
Total Synthesis of Cephalosporolide F
Machine Learning-Guided Synthesis of Clovane Sesquiterpenoids
Переглядів 1,5 тис.Рік тому
Machine Learning-Guided Synthesis of Clovane Sesquiterpenoids
Synthesis of (±)-Lysergic Acid
Переглядів 7 тис.Рік тому
Synthesis of (±)-Lysergic Acid
Total Synthesis of Portimine A and B
Переглядів 1,9 тис.Рік тому
Total Synthesis of Portimine A and B
Enantioselective Synthesis of (+)-Lucidumone
Переглядів 1,8 тис.Рік тому
Enantioselective Synthesis of ( )-Lucidumone
Total Synthesis of Atrachinenins A and B
Переглядів 1,3 тис.Рік тому
Total Synthesis of Atrachinenins A and B
One-Step Total Synthesis of Peshawaraquinone
Переглядів 1,8 тис.Рік тому
One-Step Total Synthesis of Peshawaraquinone
Total Synthesis (E) and (Z)‑Ocellenyne
Переглядів 2 тис.Рік тому
Total Synthesis (E) and (Z)‑Ocellenyne
Total Synthesis of Dysiherbols A, C, and D
Переглядів 1,4 тис.Рік тому
Total Synthesis of Dysiherbols A, C, and D
Total Synthesis of (−)-Peyssonnoside A
Переглядів 1,8 тис.2 роки тому
Total Synthesis of (−)-Peyssonnoside A
Unified Total Syntheses of Benzenoid Cephalotane Norditerpenoids
Переглядів 1,7 тис.2 роки тому
Unified Total Syntheses of Benzenoid Cephalotane Norditerpenoids
Synthesis of Pleuromutilin
Переглядів 2,4 тис.2 роки тому
Synthesis of Pleuromutilin
Synthesis of Pleurotin
Переглядів 4,2 тис.2 роки тому
Synthesis of Pleurotin

КОМЕНТАРІ

  • @wiktormazur7027
    @wiktormazur7027 17 годин тому

    Why in 2:55 second reaction is called 5-exo-trig, instead of 5-exo-tet? It is attacking sp3 carbon or am i mistaken

  • @ppbonner3816
    @ppbonner3816 День тому

    best video of all time?

  • @BenjarminRS
    @BenjarminRS День тому

    Aw yee here we go

  • @UniCorneliusfan21
    @UniCorneliusfan21 День тому

    Peak cinema just dropped

  • @YourTreasure-u1b
    @YourTreasure-u1b Місяць тому

    Can we do argument on rhodium catalysis mechanism?

  • @lalayatem3758
    @lalayatem3758 Місяць тому

    Could you do a video on Danieshksy Taxol please? Your videos are amazing! God bless you

  • @YourTreasure-u1b
    @YourTreasure-u1b Місяць тому

    Your highlighted work is appreciated 👍, and I have a humble suggestion which is that if you summarize the key steps from the synthetic background or key steps from the previously published papers will be more interesting.

  • @dzhangarbadmaev1057
    @dzhangarbadmaev1057 3 місяці тому

    Another excellent minilecture! I tried to dissect a total synthesis paper on my own recently, and kept thinking that I would have had a much better time if you had explained it every step of the way. Super happy you're making these lectures, keep it up!

  • @UniCorneliusfan21
    @UniCorneliusfan21 3 місяці тому

    Man I already seen all of them sob

  • @nikolashadjipaschalis5629
    @nikolashadjipaschalis5629 3 місяці тому

    Wake up guys new total synthesis just dropped!

  • @Demon-pb5jm
    @Demon-pb5jm 3 місяці тому

    What a fabulous channel

  • @nuria4459
    @nuria4459 3 місяці тому

    Hi! Nice video! I have a question. Why after the claisen condensation you made the noyori asymetric transfer hydrogenation?? I ask because after some steps the swern oxidation takes places so, why just reduce and protect one of the ketons normal, without quiral reactions? Congratulations again for the video :)

  • @dzhangarbadmaev1057
    @dzhangarbadmaev1057 3 місяці тому

    Excellent video! The redox fragmentation of the phthalimide to generate the alkoxy radical is also non-trivial.

  • @nuria4459
    @nuria4459 3 місяці тому

    Majestic

  • @dzhangarbadmaev1057
    @dzhangarbadmaev1057 4 місяці тому

    Thank you for taking the time to make such instructional videos!

  • @KrashFries
    @KrashFries 4 місяці тому

    2:48 the chromate ester elimination produces a Cr(IV) species, which should have the nominal formula H2CrO3. note that Cr(IV) is unstable and tends to decay to Cr(III) and eventually solid Cr2O3 (ask the solid state chemists or nanochemists about that mechanism, i’m out).

  • @skyethebi
    @skyethebi 4 місяці тому

    2:07 shouldn’t methylephedrine contain a benzene ring

  • @samjo475
    @samjo475 4 місяці тому

    at 8:08 I think is should be PPh3 and not Ph3

  • @Chemicator
    @Chemicator 4 місяці тому

    What a fascinating structure! Perfect explanation.👍🧪

  • @aidanlooby
    @aidanlooby 4 місяці тому

    It has been a few months now and I am still not over this synthesis! The fulvene chemistry is absolutely crazy and using a Heck reaction to essentially close the tetracyclic core is amazing. Love the channel!

  • @UniCorneliusfan21
    @UniCorneliusfan21 4 місяці тому

    It’s a good day when simplifying synthesis uploads Also I think the thionyl chloride elimination should proceed via the hemiacetal oxygen attacking thionyl chloride instead of the open chain form alcohol

  • @Reaboian
    @Reaboian 4 місяці тому

    Oh the one synthesis workshop did a podcast on, this is a really typical and cute molecule

  • @dzhangarbadmaev1057
    @dzhangarbadmaev1057 5 місяців тому

    Please don't stop doing what you're doing. Your effort is highly appreciated!

  • @samirrezgui3680
    @samirrezgui3680 5 місяців тому

    💯💯💯🔥🔥🔥

  • @ja-ja-eldorado
    @ja-ja-eldorado 5 місяців тому

    hey hows things .. i heard that special K hydrochloride is one of the hardest chemicals to make. is it??.. do you no how to synthesis it ??.. for educational purposes of course .. but do you.. im here in glasgow i used to get it for micro dosing for anxiety and it worked a treat.. now cant get any and all thats going about is this esketamine witch only effects the mind not the body.. cause i heard a few years back the patent ran out for k-hydrochloride so every one of the pharma co-op's make a K substitute or pre log.. cause who ever owns the patent now is not letting any other chemist or pharma company use it.. but id love to see the proper stuff again.. same with PCP .. i was born in 86 so i missed all that scene and never tried it.. would love too lol.. anyway good work and good vids.. im so interested in chemistry but self taught.. so just about got the just of it.. but id love to see a real chemist at work.. im a chef to trade and i gees its kinda the same just diff ingredients.. if you want to chat more in depth let me no and ill give you my email ... blessings ..

  • @diegomontalvo9173
    @diegomontalvo9173 6 місяців тому

    dope

  • @KevinChen-u2n
    @KevinChen-u2n 6 місяців тому

    At around 7:20 about the Beckmann Rearrangement, the HOMO is not actually the C-C sigma bond. It's just the transcoplanar arrangement of this bond and the N-O bond that makes the reaction happen.

  • @UniCorneliusfan21
    @UniCorneliusfan21 6 місяців тому

    It’s always a good day when simplifying synthesis uploads We aza, cope, mannich!

  • @BaitingSimulator
    @BaitingSimulator 6 місяців тому

    Im working on a fairly complex polyketide myself but wouldn't have come up with that strategy in weeks of daily brainstorming. Highly condensed alkaloids are a treasure trove of genius ideas put to the test.

    • @SimplifyingSynthesis
      @SimplifyingSynthesis 6 місяців тому

      The Stoltz group never disappoints. Their synthesis of Ineleganolide is one of my all time favourites

    • @UniCorneliusfan21
      @UniCorneliusfan21 6 місяців тому

      What is the name of the molecules you’re working on? If you can’t disclose the name, In this molecule, how many 1. ACQC (all-carbon quaternary centers) are there, how many of which are contiguous? 2. Stereocenters, of which how many are contiguous? 3. Neopentylic positions 4. Heteroatoms And what’s the cyclic framework like, if any? :3

  • @r9341-tss1
    @r9341-tss1 6 місяців тому

    I spent my masters degree working on a total synthesis. It didn't work, but it really has given me an appreciation for the work it needs. That cascade at the end was very elegant and I could only wish to see those disconnections. Just a side question, with aryl diazoniums to aryl azides - doesn't this usually proceed via the pentazole?

    • @SimplifyingSynthesis
      @SimplifyingSynthesis 6 місяців тому

      Just read up on that (Chem. Commun., 2015, 51, 8954-8957), it appears you are correct. I wasn't aware of that mechanism, thanks!

    • @UniCorneliusfan21
      @UniCorneliusfan21 5 місяців тому

      Infact the 2-aza cope mannich cascade could also be thought of as firstly a iminium formation, then an alkene attacks the iminium and then subsequent pinacol-type ring expansion if your not good with 3,3 sigmatropic rearrangements This was a mistake I made helping someone with mechanism problems, the stereochemistry will definitely be different if you think of it that way (ring expansion is guaranteed to be stereoinvertive)

  • @exuma7524
    @exuma7524 6 місяців тому

    Yay new Simplifying Synthesis vid

  • @alexandervonzoller-sakharo6386
    @alexandervonzoller-sakharo6386 6 місяців тому

    Very clever analysis. I doff me hat to ye, lad.

  • @kurz-Stibi
    @kurz-Stibi 6 місяців тому

    It is Queen englis thanks I can understand was afraid of indian english but every queen english chemistry explaination channel is worth to be recomended. Just like with Prof dave explains.

  • @pauldietz1325
    @pauldietz1325 7 місяців тому

    Micromolar is not a low concentration for drug candidates.

  • @UniCorneliusfan21
    @UniCorneliusfan21 7 місяців тому

    Naw electrochem jumpscare 😭

  • @balls345
    @balls345 7 місяців тому

    Very nice synthesis, as per usual from the Baran group

  • @azertyuiop432
    @azertyuiop432 8 місяців тому

    It would be interesting to see if anti microbial activity is increased with the legthening of the macrocyclic framework ; althought maybe because of the probable non-linearity of a pure aliphatic legthening, the molecule would adopt an inefficient conformer

  • @matthewvonbargen9450
    @matthewvonbargen9450 8 місяців тому

    That DIBAL-H mechanism at 4:48 needs to be reworked. An electrophilic aluminum species (with an unoccupied p orbital) does not deliver a hydride to a carbonyl directly. It is a 2 step process (Lewis acid-base coordination of the C=O L.P. to the p* of the Al, then intramolecular hydride transfer of the corresponding adduct) It may sound like I am being pedantic, but I have numerous friends from numerous schools who have gotten this exact mechanism wrong (and in some cases chastised) by drawing it the way you have it in the video.

    • @UniCorneliusfan21
      @UniCorneliusfan21 8 місяців тому

      your correct although they're probably doing it for simplicity

  • @UniCorneliusfan21
    @UniCorneliusfan21 8 місяців тому

    damn that Au catalyzed alkyne rearrangement though that was really cool allenes really do need to be used more often in synthesis, I rarely find them being used as intermediates these days

  • @NonTwinBrothers
    @NonTwinBrothers 8 місяців тому

    Thank you max miller

  • @jdspharmacopeia
    @jdspharmacopeia 9 місяців тому

    Do you have a simpler molecule beginner video 😂

  • @user-mp4bc9qp2x
    @user-mp4bc9qp2x 9 місяців тому

    i'm not sure if they cover this in the paper, but is there a reason they want to administer a prodrug at all? why not just give the API and you wouldn't have metabolism issue etc.

  • @RalfStephan
    @RalfStephan 9 місяців тому

    There is still the question if a shorter psilocin exposure can have the same therapeutic effect, which I doubt

    • @nervonabliss
      @nervonabliss 9 місяців тому

      I think that will depend on the setting and application of therapy. I believe determining what will be most efficient for each individual patient will be more difficult.

  • @RalfStephan
    @RalfStephan 9 місяців тому

    Very informative about the lab methods used in this type of research, many thanks

  • @chemistrycapital
    @chemistrycapital 9 місяців тому

    Saw this article a while ago. It's great that you've made an easy to understand video on it!

  • @priyotoshdas225
    @priyotoshdas225 10 місяців тому

    Fantastic demonstration !🎉 A small typo: in any of first few slide where Negishi coupling mechanism has been shown, there after transmetallation it should take tosylate upon exchange not triflate. In short, it should be ZnBr(OTs) rather than ZnBr(OTf).

  • @shankhajitmondal183
    @shankhajitmondal183 10 місяців тому

    In the polycyclic system Hydrogen is behind the plane?? Benzyl gr also followed the same position.

  • @shankhajitmondal183
    @shankhajitmondal183 10 місяців тому

    So beneficial video. Please keep posting more and more. It will help students like me to build up ideas of how to design organic synthesis.

  • @shankhajitmondal183
    @shankhajitmondal183 10 місяців тому

    Hi so nice explanation. Is there any explanation for stereoselectivty of the Tsuji-Trost reaction?? Last HAT step why H added to right hand side??

  • @stevengill1736
    @stevengill1736 10 місяців тому

    When you look at the complexity of the receptor proteins, it's absolutely astounding how everything in biochemistry works so well!