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.
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
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 :)
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.
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?
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)
Please don't stop doing what you're doing. Your effort is highly appreciated!
It’s always a good day when simplifying synthesis uploads
We aza, cope, mannich!
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.
The Stoltz group never disappoints. Their synthesis of Ineleganolide is one of my all time favourites
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
💯💯💯🔥🔥🔥
Yay new Simplifying Synthesis vid
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 :)
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.
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?
Just read up on that (Chem. Commun., 2015, 51, 8954-8957), it appears you are correct. I wasn't aware of that mechanism, thanks!
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)