Dirk Trauner
@dirktrauner.bsky.social
Penn Integrates Knowledge Professor, Natural Product Aficionado, Photopharmacologist, Fox Terrierist, Book Lover, and Unfulfilled Architect. #firstgen
Thelepogine! Congratulations to Matt and Christoph on bringing this one home! I’m very fond of the final result. pubs.acs.org/doi/10.1021/...
Total Synthesis of the Diterpene Alkaloid Thelepogine through Enyne Hydroamination
The total synthesis of the atypical diterpene alkaloid thelepogine is reported. Our pathway features the asymmetric construction of a carbotricyclic intermediate that undergoes a 2,3-Wittig–Still rear...
pubs.acs.org
Exited to speak at ISOP 2026 in Groningen next week about making Photoswitches and putting them to good use. isop2026.eu
ISOP 2026
ISOP 2026 Symposium Website
isop2026.eu
Stephadiamine, take two. A second synthesis is justifiable if you (a) radically change the strategy and (b) develop new methodology along the way. Congratulations, Ana Vi, on bringing this one home! pubs.acs.org/doi/10.1021/...
Concise Synthesis of (±)-Stephadiamine via Vinylogous Wenker Cyclization
A short and diastereoselective synthesis of stephadiamine is presented. The carbocyclic framework of the alkaloid was built in the opening step through a homoconjugate addition–Wittig olefination cascade with a modified Schweizer–Fuchs cyclopropyl phosphonium salt. The challenging aza[4.3.3]propellane was subsequently installed through a vinylogous substitution of an allylic hydroxy group with a primary amine that was developed for the purposes of the synthesis. After a series of oxidations, a second α-tertiary amine was introduced through a diastereoselective Strecker reaction, thus establishing the syn-diamine motif. Finally, an undesired retro-Strecker pathway was circumvented by using an azide functionality to mask the primary amine during a late-stage lactonization, thus enabling the completion of the synthesis in 12 steps.
pubs.acs.org
Silyl protecting groups can function as dispersive directing groups, leading to unexpected stereoselectivities! Collaborating with Robert Paton, we have demonstrated this for a specific case. Stay tuned for a more systematic study! pubs.acs.org/doi/full/10....
Protecting Groups as Dispersive Directing Groups: Toward the Asymmetric Synthesis of Altemicidin
We report progress toward the asymmetric total synthesis of altemicidin, a monoterpene alkaloid featuring a 6-azatetrahydroindane core. A diastereoselective 1,3-dipolar cycloaddition with TMS-diazomethane enabled the construction of a key pyrazoline intermediate. Computational analysis (EDA/NCI) revealed attractive London dispersion forces as the origin of the unexpected stereoselectivity. An effective method to convert the initial silylated 1-pyrazoline into a stable 2-pyrazoline was developed. Selective reductive trifluoroacetylation and SmI2-mediated N–N bond cleavage afforded a 1,3-diamine suitable for further functionalization.
pubs.acs.org
Vitamin D is famous for its photochemistry. We have now added a photopharmacology aspect in a wonderful collaboration with the Merk group. onlinelibrary.wiley.com/doi/full/10....
An Agonist/Antagonist Photo‐Switchable Vitamin D Mimetic Enables Bidirectional Optical Control of VDR
Vitamin D exhibits complex and cell-specific biological effects in multiple tissues via activation of the ligand-sensing transcription factor vitamin D receptor (VDR). The photo-switchable vitamin D ...
onlinelibrary.wiley.com
What a week end at Penn! First we were honored to host Roald Hoffmann and then we ran the Chemistry 5K. La Vita e Bella.
A big step forward in Photopharmacology, just published in Nature Medicine: nature.com/articles/s41... A compound we conceptualized in 2008 (PMCID: PMC4040390) and synthesized in 2010 (PMCID: PMC3401033) proves effective in human vision restoration.
Intravitreal photoswitch therapy in advanced retinitis pigmentosa: a phase 1 open-label trial - Nature Medicine
A first-in-human phase 1 trial shows that intravitreal photoswitch therapy can be administered safely in advanced retinitis pigmentosa, with exploratory signals compatible with light responsiveness fo...
nature.com
Excited to deliver the Overman Lecture next Wednesday at UC Irvine!
Opticial Control of Cholesterol, attempting to stay as close to the original as possible. Congratulations to Michael Zott, who defined and spearheaded this study, and to our wonderful collaborator Luca Laraia!
Luca Laraia@lucalaraia.bsky.social · 8mo agoDelighted to have collaborated with the @dirktrauner.bsky.social lab on the development and characterisation of #photoswitchable #cholesterol derivatives, now out in @jacs.acspublications.org! (1/3) pubs.acs.org/doi/full/10....
Delighted to have collaborated with the @dirktrauner.bsky.social lab on the development and characterisation of #photoswitchable #cholesterol derivatives, now out in @jacs.acspublications.org! (1/3) pubs.acs.org/doi/full/10....
Development of Photoswitchable Cholesterol Derivatives through Side Chain Replacement
Cholesterol is ubiquitous in biology, shaping membrane properties and serving as a biosynthetic precursor for essential signaling molecules and hormones─and, in some contexts, acting as a signaling mo...
pubs.acs.org
[6+4] Cycloadditions! Introducing our first dive into this fascinating subject in a very enjoyable collaboration with Ken Houk and his team. Congrats to Harrison and Tufan! pubs.acs.org/doi/10.1021/...
Synthesis of Collinoketones via Biomimetic [6 + 4] Cycloaddition
Cycloadditions are among the most powerful reactions for constructing molecular complexity. The archetypal example is the [4 + 2] (Diels–Alder) cycloaddition, which efficiently furnishes cyclohexene d...
pubs.acs.org
As my memory is not as good anymore as it once was, I am excited to share this exciting collaboration with Cristina Alberini (NYU) with you: www.nature.com/articles/s41...
A prodrug targeting CIM6P/IGF2R enhances memory in healthy mice and reverses deficits in an Angelman syndrome mouse model - Translational Psychiatry
Translational Psychiatry - A prodrug targeting CIM6P/IGF2R enhances memory in healthy mice and reverses deficits in an Angelman syndrome mouse model
nature.com
It has been quite an emotional week for me — first, reconnecting with my Berkeley past, and then looking to the future by celebrating with my former graduate student Nina Hartrampf. Congrats, Nina, and, yes, "Peptide können alles!"
Helvetica Chimica Acta@helvchimacta.bsky.social · 9mo ago@ninahartrampf.bsky.social gives the award talk (@dechema.bsky.social prize 2024) ‚Flow-Based Synthesis of Post-Translationally Modified Peptides and Proteins‘ at the #UniZH. Congratulations to our ECAB member!!
It was wonderful to return to UC Berkeley and deliver a lecture with Clayton Heathcock in the audience.
Thrilled to return to UC Berkeley for the Clayton Heathcock Lecture on November 4!
Excited to share our new @pubs.acs.org paper! We engineered cells with ~10% photolipids in the ER membrane. This enabled optical control of membrane viscosity to study its impact on ER→Golgi protein transport. @dirktrauner.bsky.social @noemijimenezrojo.bsky.social pubs.acs.org/doi/10.1021/...
Optical Control of Membrane Viscosity Modulates ER-to-Golgi Trafficking
The lipid composition of cellular membranes is highly dynamic and undergoes continuous remodeling, affecting the biophysical properties critical to biological function. Here, we introduce an optical a...
pubs.acs.org
Just out: Our collaboration with Eric Schelter & Randall Wilharm on parsing the fascinating photochemistry of lanthanides with azobenzene photoswitches. A deep dive into light and rare earths en route to more efficient separations. pubs.acs.org/doi/10.1021/...
Breaking a Lewis Acidity Trend for Rare Earths by Excited State Quenching
Facilitating different chemistries between the rare earth (RE = La–Lu, Sc, Y) ions is of significant interest for their separations. While the bulk of attention has been on maximizing the small differ...
pubs.acs.org
Greetings from the GRC on Artificial Molecular Switches and Motors! It’s exciting to see how the field has grown and is moving toward everyday applications—think photoswitchable tattoos!
I love the Hoya carnosa in my office climbing on polytwistane.
I had a great time at the University of Rochester as the Victor Chambers Lecturer! And I really enjoyed the amazing George Eastman House and Museum, built by a millionaire (nowadays billionaire) who was civic minded and kept a low profile.
We have updated our "Chemical Neuroscience" course to include pentameric ligand-gated channels and the first GPCRs. www.traunergroup.org/teaching
Check out our approach toward disciformycin and gulmirecin, spearheaded by Peter Ruehmann @nyuchemistry. pubs.acs.org/doi/10.1021/...
Ready to take off as a synthetic chemist? Check out this tutorial review we wrote with Frank Glorius and Jasper Tyler!
Frank Glorius@gloriusfrank.bsky.social · last yr.Scholarly review written by @DirkTrauner and @GloriusGroup: Reaction development: a student's checklist📜☑️😀 Published in Chem. Soc. Rev. doi.org/10.1039/d4cs...
I am teaching my favorite course again this semester: "Chemical Neuroscience - a Synthetic Approach". We are posting some materials online, check them out. www.traunergroup.org/teaching
Dearomative Diels-Alder reactions are currently hot in total synthesis. They go back to Peter Yates (who trained my mentor Sam Danishefsky). And the Wessely reaction was also discovered in Vienna :)
