Our group was recently selected to receive a small external grant from Organic Syntheses, Inc. Only 12 of these are given out each year, and many past award recipients are among the more well-known names in the field of synthetic organic chemistry at primarily undergraduate institutions (PUIs) in the United States. The Organic Syntheses, Inc. PUI faculty grant for research will fund our research efforts during Summer 2022 and Summer 2023. Specifically, it provides a $5,000 stipend each year to compensate a full-time undergraduate who will work under the title of Organic Syntheses Summer Scholar and money for supplies, reagents, and equipment. I have chosen UVU undergraduate Morgan Payne as the recipient of this fellowship for Summer 2022. He will be working on the preparation of halogenated derivatives of clavatadines A-E. Congratulations Morgan!
Congrats to Kylee Maxfield and Morgan Payne for their contributions to our recently completed research article, which we uploaded to the preprint server ChemRxiv (pronounced “Chem-ar-KIVE” at the following link:
Although this version of the paper was not peer reviewed, we also submitted it to a reputable journal in the field to undergo peer review, and I’ll post an update once it gets published. By far, this was the longest paper I’ve written, and the first to include National Cancer Institute NCI-60 screening data on our synthesized compounds. All told, it was a herculean effort. Much credit goes to the students who devoted so much of their time in the lab and in the NMR instrument room to make it all happen. Thanks also to the sabbatical leave I was given this year, which enabled me to spend an enormous amount of time in the lab free of teaching duties.
Kylee Maxfield and I drove down to St. George, Utah in late February to visit Dixie State University for the 2022 Utah Conference on Undergraduate Research. There, she presented a 15 minute talk on our group’s recently completed total synthesis of the natural products clavatadine C and clavatadine D. Quite a few UVU students attended as well, and contributed talks as well as poster presentations.
This was my first UCUR conference. I usually opt out of the local-level events in favor of the really impactful national meetings. This year, however, I started encouraging students to go to local meetings for the experience and when the timing enables them to use it as practice for a bigger meeting. An additional benefit of local meetings is the lower cost to attend for both faculty and students. We’ll definitely be participating at UCUR in future years.
More recently, Kylee and I returned from San Diego where we ventured to the American Chemical Society spring national meeting. It is the first ACS meeting I’ve been able to attend in person since 2018, and Kylee’s first (and probably last). Kylee gave an updated version of the clavatadine C and D talk she gave at UCUR and added in our clavatadine E synthesis results as well. She was one of only two undergraduates in her session to present talks; both had recently graduated. Luckily, Kylee’s husband Brady was able to attend her talk too. Here’s a picture of us at dinner together. Although I’m grateful for the new wide-angle lens on the newer iPhones, the camera definitely adds more than 10 pounds near the edges. A photo of Kylee taken during her talk follows.
Two other UVU chemistry students presented at the meeting, and UVU Chemistry faculty member Dr. Sally Rocks also travelled with us and presented a talk on our collaborative Structure Determination course for senior undergraduates.That has been a fun course to team teach with other UVU faculty. I teach three weeks of both the lab and lecture section. We focus on how to use 1-D and 2-D NMR spectroscopy to establish atom connectivity in small organic molecules. Another section highlights errors in structure determination and how to use computational (computer-based) methods to predict and confirm structure.
Finally, I gave two talks in person. The first was an invited lecture and panel discussion as part of the special Division of Organic Chemistry symposium titled “Successful Products and Models of Undergraduate-Based Research: Good Science, Better Scientists.” There, I had the opportunity to speak alongside two alumni from UC Irvine: Carolyn Anderson and Tim Clark. Tim and I were both in Keith Woerpel’s group. The second talk covered our group’s published total synthesis of clavatadine B from 2019. I’ve been trying to give this talk in person for two years, but ACS meetings since then were either cancelled or held virtually due to COVID.
Special thanks to the ACS Division of Organic Chemistry, who selected me to receive a $600 PUI Faculty Travel Grant to attend this meeting, and who sponsored the entirety of my travel costs as a result of my participation in the invited “Successful Products” symposium.
Yes, yes, I know, that in my 13th year of teaching I should be embarking on my second research sabbatical; however, the needless, surprising, and traumatic mid-career job change I experienced as my first sabbatical would begin postponed it until now. Thanks, but no thanks, Central Washington University Chemistry Department!
What’s weird at UVU is that research sabbaticals are not automatically approved and few people actually take them. Because the focus here so heavily emphasizes teaching, even qualified and correctly timed applications may not go forward if it would place too much of a teaching burden on their department. Fortunately, no one else in my department applied this year, yet I was not alone in being eligible.
Instead of taking a sabbatical “leave”, I’ll be staying at UVU. Now I’ll have time to work on my research projects in my shared lab space and might be able to mentor a few students too. Although I want to do an external sabbatical, I felt I should solidify my research position and complete and publish my current projects before working on someone else’s research agenda. I’ll admit, it’d be exciting to do a tandem teaching and research sabbatical with Neil Garg at UCLA, do some amazing synthesis work at Harvard (Myers, Jacobsen, Shair), Scripps (Baran, Yu, Shenvi), Caltech (Sarah Reisman), Cal (Richmond Sarpong), or Utah (Ryan Looper) to mention a few, or travel to Australia to do some deep-sea diving and natural product isolation/identification with Ronald Quinn, a research collaborator on our clavatadine A project. Another part of my sabbatical leave will allow me to dedicate time to create a chemistry-focused history/philosophy/political science course for the UVU Honors Program. Leading a small, honors-style course that focuses on reading, in-class discussions, and projects has been a dream of mine since I began teaching. Finally, I’ll hopefully be able to write manuscripts on a pedagogical research project I’ve been working on for a few years now and also a couple of articles describing some in-class activities and assignments that seem suitable for the Journal of Chemical Education.
Finally, looking forward to the future, I re-submitted the abstract that I planned to give at the Spring 2020 ACS meeting that was cancelled. The ACS announced that their Fall 2021 meeting in Atlanta will be in-person. As I prepared the abstract for submission, I believe I checked the box that said, “Present in person even if my division is only offering virtual presentations.” Now that I’m fully vaccinated, I’m ready to rejoin my community and declare a moratorium on my personal boycott of virtual meetings.
The recently reported and growing epidemic known as COVID-19 sounds terrifying. We still know so little about the disease, such as how it’s transmitted, whether it’s airborne, how deadly it is, and the short- and long-term health effects of what seems like no normal cold virus. For now, because so much about the virus is uncertain and local universities are shutting down in-person activities, we’re taking the unprecedented step of halting in-person research. Thus, the progress we’ve made on the total synthesis of clavatadine C, D, and E will have to wait for a while. We hope to resume research in a month or so depending on how long the pandemic lasts. There’s talk about developing a vaccine, but that could take years. Are we in for a long, dark period of our lives, or will this all blow over in short order? Who knows?
Earlier, I posted that I’d been accepted to give an oral presentation at the 2020 Spring ACS meeting, but the ACS just made the (literally) unprecedented step of cancelling the meeting entirely with just one week remaining until it was scheduled to begin. I checked, and this is the first time the ACS has ever cancelled their national meeting. ACS meetings endured through World War I, World War II, but could not survive COVID-19. I’m sure I was not alone with the burden of having to cancel all air travel, hotel accommodations, and the like, but boy is this frustrating. It sounds like they’re also going to cancel the 2020 BCCE meeting to which I had submitted two abstracts. When will this end?!
For those in situations such as this, where we’ve had abstracts accepted but through no fault of our own the organizers decided to cancel the meeting, what do we do? Do we leave the items on our CV with a note that the conference was terminated? I think that sounds the most fair and is what I’ll do. But what do you think?
Congratulations to UVU graduates Michael Davenport, Jordan Dickson, and Matthew Johnson! Each earned their first peer-reviewed publication in the Journal of Natural Products. We report the first total synthesis of clavatadine B, a natural inhibitor of human blood coagulation factor XIa. Though it is not as potent as the clavatadine A congener, its synthesis was achieved using a similar direct, early-stage guanidinylation approach. The total synthesis originated from the same dibrominated precursor that was used to make clavatadine A, which made the total synthesis four-steps long. It is six steps from commercially available materials.
Read our paper here: Total Synthesis of Clavatadine B
With three abstracts submitted for Spring and Summer 2020 conferences, it looks like it’s going to be an active year for our group. Specifically, we submitted an abstract to give an oral presentation at the 2020 Spring ACS meeting, which was just accepted! Steve Chamberland will give the talk, which will focus the adventure and lessons learned on the path to our recently completed total synthesis of clavatadine B. This summer, he plans to give two talks at the Biennial Conference on Chemistry Education, the BCCE, which will be held at Oregon State University. There, we hope to meet up with two Chamberland group alumni, Jacob Buchanan and Chris Malmberg. Jacob recently finished his Ph.D. at Oregon State and is now working in industry and Chris is in the final stretch of his Ph.D. journey. Dr. Chamberland’s talks will focus on the Chemistry Cornerstone courses he developed at UVU and an in-class activity involving the seminal (15-step!!!) total synthesis of (+)-ryanodol by Caltech Professor Sarah Reisman and co-workers. This class discussion in Chemistry 2320 (Organic Chemistry II) normally falls during Women’s History Month, and highlights not just the work of a female chemist, but the work of one of the titans of modern synthetic organic chemistry.
This summer Steve attended the Biennial Conference on Chemistry Education (BCCE), which was held at the University of Notre Dame in South Bend, Indiana, as well as the fall national meeting of the American Chemical Society in Boston. He presented three talks at those conferences about recent metacognition research in organic chemistry as well as a classroom demonstration. The presentation titles are “The Metacognitive Exam Tool to Help You Learn (METHYL) project for sophomore organic chemistry,” and “Creating CSI experts in NMR analysis: an engaged, group-inquiry exercise in spectroscopy.”
Traveling to Boston for the ACS meeting offered an opportunity to join a T. Ross Kelly research group alumni reunion from Boston College. Ross was Steve’s undergraduate research mentor, and is in the middle-left of the picture. Twenty years ago, Steve completed the first total synthesis of luotonin A, a pyrroloquinazolinoquinoline natural product, with Ross and post-doc Rich Silva!
Since then, the BC men’s ice hockey team won a few national championships, and it was nice to see the banners hanging from the rafters in Conte Forum.
In addition, Steve’s Ph.D. advisor, NYU Professor Keith A. Woerpel (formerly of UC Irvine), was awarded a prestigious ACS Cope Scholar Award for his explorations of stereoselective reactions involving oxocarbenium ions. The X-ray crystal structure of an axially-substituted six-membered ring dioxocarbenium ion from Steve’s 2005 JACS paper was featured in the award address. It was great to catch up with a few group alumni from the early 2000s.
This April, albeit four years later than expected, Steve was awarded tenure with promotion to the rank of associate professor. It becomes official on July 1, which is when he plans to exhale for the first time in ten years. He couldn’t have navigated the extreme ups and downs of the process without his dear wife, pictured below at the tenure recognition dinner in April.