@GustafsonLab

Asymmetric Synthesis and Chemical Biology

 San Diego, CA
gustafsongroup.sdsu.edu/wordpress/
Joined June 2017
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We did a thing! pubs.rsc.org/ob/article/doi/… This review, which is part of a themed collection on axially chirality, was written with the goal of sharing some fundamentals and capturing a 'snapshot' of the state of atropisomerism in drug discovery.

A practical guide to atropisomerism: fundamentals and case studies from modern drug discovery

Atropisomerism is a form of axial chirality that arises when rotation about a single bond is sufficiently restricted to render the enantiomeric conformers

pubs.rsc.org
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One thing worth mentioning is the majority of examples utilized tried and true chiral resolution chemistry, however there was a lot of innovation in recycling of the unwanted atropisomer. There were also a few examples of asymmetric catalysis being employed.
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We hope people find this useful, and it helps stimulate discussion and thought on how best to set atropisomeric axes in practical settings.
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Excited to announce that the preliminary program for the 2027 Gordon Research Conference on Heterocyclic Compounds, June 20–25 in Newport, RI, is online! grc.org/heterocyclic-compoun… We have an outstanding lineup of academic and industry scientists. Hope to see many of you there!
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You forgot to mention the PhD's beat the PhD Candidates in volleyball
Lipshultz Group@LipshultzSBUJul 9
a successful beach day (most) of the organic chemistry groups along with a PhDs vs Candidates volleyball match! (a few injuries, no deaths) @GustafsonLab @jillalty @barneygrubbs @QJBruch Prof. Katherine Aubrecht and Prof. Matthew Parkers Group
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Another day another preprint on ChemRxiv! “Leveraging Atropisomerism to Obtain a Mutant-Selective c-KIT Inhibitor in Gastrointestinal Stromal Tumors” A story of privileged heterocycles, atropisomerism and kinase selectivity. chemrxiv.org/doi/full/10.264…

Leveraging Atropisomerism to Obtain a Mutant-Selective c-KIT Inhibitor in Gastrointestinal Stromal...

Atropisomerism is a stereochemical phenomenon that is becoming increasingly prevalent in the modern drug discovery endeavor. A significant portion of small molecule drugs, including the FDA-approved...

chemrxiv.org
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The R-atropisomer* maintained potency against cellular models of GIST (IC50 < 10 nM) while displaying improved target selectivity, including towards key oncogenic c-KIT mutants. *Cahn-Ingold-Prelog priorities cause the analogs to have opposite stereochemical descriptors.*
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The S-Atropisomer* had no KIT activity, but displayed intriguing selectivity towards LYN kinase, an emerging target for the treatment of cancer, autoimmune diseases and inflammatory conditions, that currently lacks highly selective inhibitors.
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Excited to share our new ChemRxiv preprint: “Leveraging Conformational Control of Neratinib’s C–N Axes to Enhance HER4 Selectivity in Ovarian Cancer” congrats to the tam @StonyBrookChem and @SDSUChemBiochem Read here: doi.org/10.26434/chemrxiv.15…

Leveraging Conformational Control of Neratinib’s C–N Axes to Enhance HER4 selectivity in Ovarian...

Diarylamines are among the most privileged scaffolds in drug discovery, with a myriad of examples in the clinic including the multi-kinase inhibitor neratinib which possesses indications towards HER2...

chemrxiv.org
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The ‘conformational mapping’ of diarylamine crystal structures suggested that the pan-HER kinase inhibitor neratinib adopts two planar conformations around a C–N axes (similar to cis and trans alkenes). HER family kinases generally preferred the ‘trans’ conformation
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This led us to introduce a peri Fluoro group as a H-bonding handle to ‘lock’ that axis into the trans conformation. This seemingly simple modification led to a dramatic increase in HER selectivity, particularly towards HER4, a kinase with emerging implications in ovarian cancer.
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The final version of this manuscript is up at @ACSCatalysis pubs.acs.org/doi/10.1021/acs…

A Rh(II)-Catalyzed Atropisomer Selective Ring Expansion of 3‑Aryl Indoles to 4‑Aryl Quinolines

Abstract. Heterocycles containing stereogenic axes are becoming increasingly important throughout the drug discovery endeavor, and methodologies that provi

pubs.acs.org
Gustafson Group @ Stony Brook@GustafsonLab8 Apr 2025
I am sharing this preprint from my group. Inspired by all the great recent skeletal editing work, we developed an atropisomer selective strategy to take Indoles to quinolines. chemrxiv.org/engage/chemr...
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Gustafson Group @ Stony Brook retweeted
Jeff Lipshultz@jeflipFeb 23
Our department (@StonyBrookChem) is looking for a PRODiG+ fellow – the appointment is two years, followed by conversion to a tenure-track assistant professor at the conclusion of the fellowship. A unique opportunity! apply.interfolio.com/178732
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Reposting. One more week until the deadline!
Gustafson Group @ Stony Brook@GustafsonLab1 Oct 2025
The Stony Brook Chemistry Department is searching for a Chemical Biologist at the Associate or Full professor Level. Come join us on Long Island and do some great science! apply.interfolio.com/174211
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Gustafson Group @ Stony Brook retweeted
NaOH Bartfield, PhD 🧪@NaOHBartfield16 Oct 2025
Doctor Gavin Rustin we salute you
Gustafson Group @ Stony Brook@GustafsonLab16 Oct 2025
Check out our latests work in collaboration with @Taylorlab_Chem ! We evaluated their biomolecular photocaged trifluormethylation reagent on small molecules, finding it effected the rapid trifluoromethylation of diverse aromatics, including several APIs. chemrxiv.org/engage/chemrxiv…
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Check out our latests work in collaboration with @Taylorlab_Chem ! We evaluated their biomolecular photocaged trifluormethylation reagent on small molecules, finding it effected the rapid trifluoromethylation of diverse aromatics, including several APIs. chemrxiv.org/engage/chemrxiv…
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The Stony Brook Chemistry Department is searching for a Chemical Biologist at the Associate or Full professor Level. Come join us on Long Island and do some great science! apply.interfolio.com/174211
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Gustafson Group @ Stony Brook retweeted
Organic Syntheses@OrgSynth24 Sep 2025
Professor Jeff Gustafson (Stony Brook University, @GustafsonLab) (gustafsongroup.sdsu.edu/word…) presented the Organic Syntheses Lecture at Notre Dame on September 24th, 2025.
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