Brandon Wright
@B_randonwright
Followers
389
Following
2K
Media
52
Statuses
539
Chemistry PhD with @SarpongGroup at UC Berkeley ‘23 | Harvard ‘18 | Bay Area
Berkeley, CA
Joined July 2012
Grateful to the whole team and everyone who contributed along the way on this amazing journey! @AlessioReg91105 @shree_sowndarya @GuilianLuchini @NattawadeeCha11 @bobbypaton.
0
0
1
The final chapter of my PhD with @SarpongGroup at @UCB_Chemistry is published! Check out our full story of how we approached the synthesis of Daphniphyllum alkaloids inspired by molecular complexity scoring, out now in @J_A_C_S 🎉
1
17
128
RT @TotalSynthesis: Molecular Complexity-Inspired #Synthetic Strategies toward the Calyciphylline A‑Type Daphniphyllum Alkaloids Himalensin….
0
21
0
RT @NatRevChem: Molecular complexity as a driving force for the advancement of organic synthesis. A new Perspectiv….
0
7
0
Ever thought about quantifying molecular complexity? We wrote a Perspective on how modeling this fascinating concept can lead to new insights in synthetic chemistry. Check it out in @NatRevChem! 🎉. @SarpongGroup .
1
6
51
RT @SarpongGroup: Congrats to @B_randonwright on the publication of his Perspective on molecular complexity as a driving force for the adv….
0
16
0
RT @thiemechemistry: ❇️ In this Synfact of the month the @CarreiraGroup from @ETH highlighted the ‘Total Synthesis of (±)-Daphenylline’ by….
0
5
0
RT @SojungKim20: Our investigation into the photomediated ring contraction of saturated heterocycles is out in @J_A_C_S! Excited to finally….
0
18
0
RT @gloganb: Our azine N-isotope exchange is out now in @J_A_C_S! Excited to share this story with a few twists in the @SarpongGroup with t….
0
11
0
RT @SarpongGroup: Congrats to @gloganb , @SamLKraus and our collaborators at #Merckchemistry and the @Sigman_Lab on the publication of our….
0
21
0
RT @J_A_C_S: Navigating Excess Complexity: Total Synthesis of Daphenylline | Journal of the American Chemical Society @SarpongGroup. @UCBer….
0
5
0
Really lucky to work alongside such talented coworkers @AlessioReg91105 and @NattawadeeCha11 in the @SarpongGroup. Couldn't have done it without them. Congrats to the team!! 🍾.
0
0
1
Finally, we made the synthesis enantioselective with Rh catalysis. Conjugate addition of arylzinc species into this dihydropyridone worked like a charm with (S,S)-Ph-BPE as the ligand in good ee!
2
0
4
But how did this reduction mechanism work? Using deuteration studies, we learned that the hydride opens the thietane and undergoes a "reduction rebound"-type sequence to quench the resulting enolate. Raney Ni pulled off the last sulfur in the end.
1
0
5
We turned to an unexpected reaction: the thia-Paternò–Büchi! The [2+2] photocycloaddition allowed us to make a highly substituted thietane which we could then reduce down to the methyl we needed. This allowed us to finish the synthesis of daphenylline in just 11 steps!
1
0
4
Installing the methyl group was easily the hardest part. Conjugate additions and several other strategies were no-gos. We started to wonder whether a triplet biradical would help us make the C–C bond we needed.
1
0
4
Now we were faced with the ring-expansion. Heating to 250 ºC was required for promoting the 6π electrocyclic ring opening followed by a [1,5]-hydride shift to install our new distal stereocenter!
1
0
1
Starting from simple aromatic starting materials, we were able to build up molecular complexity with a series of dearomatizations. The intramolecular Rh-catalyzed Buchner gave a remarkably stable norcaradiene intermediate in only 4 steps!
1
0
4
Our total synthesis of daphenylline is out in @J_A_C_S! 🎉 Very excited to share our work in the @SarpongGroup with the community on how we navigated the challenges of this target. A brief thread 🧵#TotalSynthesis #chemtwitter
7
10
120