Sarpong Group

Several Sarpong Group members are featured in a story on College of Chemistry community members with ties to Africa!
chemistry.berkeley.edu/news/chemist...

An “Inside-Out” Strategy Enables a 14-Step Total Synthesis of Hispidospermidin Traditionally, a retrosynthesis aims to disconnect a molecular target into simpler precursors as quickly as possible, prioritizing the early deconstruction of primary contributors to the molecule’s overall structural complexity (i.e., primary complexity elements). The complementary approach, which rapidly constructs complexity early in the forward synthesis, is much less common. Herein, we report a 14-step protective group-free total synthesis of the polycyclic sesquiterpenoid alkaloid hispidospermidin, which exploits an early-stage complexity-generating bicycle formation to forge the carbon skeleton, followed by subsequent peripheral functionalizations. Specifically, a key Giese conjugate addition of a bridgehead radical established the quaternary center, and a novel isomerization was discovered, which enabled a one-pot protocol to establish the trans-hydrindane moiety, and application of a C–H desaturation/etherification sequence constructed the tetrahydrofuran moiety at a late stage. Uniquely, our strategy generates the primary complexity element, the bicyclo[3.3.1]nonane core, in the first step of the synthesis, whereas the three previous syntheses feature mid- to late-stage bicycle construction (total of 23–31 steps). Analysis of the structural complexity landscape of the four syntheses of hispidospermidin suggests that building a molecule from the “Inside-Out”, as described here, may be a broadly applicable strategy to expedite the total synthesis of topologically complex molecules.

Congratulations to Charis, Tenta and Matt, and our collaborator on structural elucidation, Dr. Settineri, on the publication of our total synthesis of hispidospermidin in JACSAu!

pubs.acs.org/doi/10.1021/...

Unified Total Synthesis of C2-Symmetric Bis(cyclotryptamine) Alkaloids Utilizing a Single-Atom Insertion/Deletion Strategy Strategies for total synthesis have advanced alongside the development of new methodologies, thereby enabling access to structurally intricate molecules that were previously difficult to obtain. Here, we present a strategy for the synthesis of bis(cyclotryptamine) alkaloids inspired by methods for single-atom insertion/deletion. To implement our plan, we first pursued the synthesis of tetrahydropsychotriadine (4), an isomer of calycanthine (1), which was achieved in 9 steps and set the stage for the preparation of calycanthine (1), chimonanthine (2), and psychotriadine (6). Our studies, driven by calculations, also provide the first access to a natural product bearing the pyrrolidinoquinoline scaffold, CPC-2 (29). Finally, we resolve a long-standing misassignment of the structure of the natural product dubbed isocalycanthine. En route to our synthesis of 4, we establish a methodology for the construction of unprecedented diaryl-substituted cis- and trans-fused 5,5-bicycles using a photodecarbonylation. The mechanism for the trans-selective formation of 5,5-bicycles is investigated by using DFT calculations.

Congratulations to Hiroki on his beautiful syntheses of bis cyclotryptamine alkaloids, now out in JACS! We are grateful to Dr. David Small for his collaboration on the computational aspects!

doi.org/10.1021/jacs...

Annulative Skeletal Diversification of Pyrimidines to Expanded Heteroaromatic Space Single-atom skeletal editing has recently emerged as a powerful strategy for the direct diversification of the heterocyclic cores of various compounds. Yet, methods that enable monocycle-to-bicycle tr...

Congratulations to team "Skeletal Annulation" (Phil, Atang, Antonia, Sam, Nicolo, and Takashi) and our collaborators Pfizer
led by @bagphos.bsky.social on the publication of our work in JACS!

doi.org/10.1021/jacs...

And here it is – Annulative Editing – aka The Monster Mash. What a super collab #PfizerChemistry & @sarponggroup.bsky.social
In 1 pot, activated pyrimidines with bis-nucleophiles like amino-pyrazoles & other small hets to deliver 6/5 hets and other useful products
#MyFirstJACS
#ChemSky #ChemChat

Excited to welcome first years Richard, David P., Nick, and David B. to the group!

Total Synthesis of Dahurelmusin A and epi-Dahurelmusin A: Effect of a Single Stereocenter Change on Biological Activity Reported herein is a total synthesis of the peptide-polyketide natural product dahurelmusin A along with its C10 epimer (epi-dahurelmusin A). The syntheses benefited from well-established aldol and macrocyclization technologies. Access to the natural product and its C10 epimer provided opportunities to test the importance of the C10 stereocenter in the biological activity of the natural product.

Congratulations to Taku and Pierre on the publication of their dahurelmusin synthesis! Thank you to Dr. Blane Zavesky, our collaborator from Corteva for going above and beyond!

doi.org/10.1021/acs....

Carbamorphine: Could This Fascinating Molecule Become The Holy Grail of Pain Relief? Since the beginning of time, humanity has searched for drugs that can relieve pain without sparking addiction or the other devastating problems tied to opioids. It’s still very early, but a UC Berkele...

Check out this highlight on our carbamorphone work! www.acsh.org/news/2025/08...

Congratulations to Dr. Richmond Sarpong (@sarponggroup.bsky.social) on being awarded the 2025 Inhoffen Medal.

This award is considered to be "the most prestigious German award in the field of natural products chemistry."

chemistry.berkeley.edu/news/richmon...

Atom-swapped morphine may help create safer painkillers By putting a carbon atom in place of a core oxygen, chemists constructed an opioid that blocks pain with less respiratory depression in mice

This beautiful work from the @sarponggroup.bsky.social also got a nice write-up in @cenmag.bsky.social

Total synthesis and biological activity of “carbamorphine”: O-to-CH2 replacement in the E-ring of the morphine core structure | PNAS Morphine is a µ-opioid receptor (MOR) agonist and potent analgesic. However, it displays several side effects including respiratory depression and ...

Behold the double-edged sword of natural product medicinal chemistry! On the one hand, doing the SAR is such a pain that industry has largely given up. On the other, look what we haven’t tapped into: a one-atom change to morphine, never before made in the 73 years since the first total synthesis!

Skeletal editing: How close are we to true cut-and-paste chemistry? Reactions that alter organic scaffolds by a single atom are already proving useful, but time will tell if they’ll fundamentally change how molecules are made

Check out this Article in @cenmag.bsky.social. News on skeletal editing that discusses some of our group's work!
cen.acs.org/synthesis/Sk...

Synthetic Studies toward the Aphidicolin Family of Diterpenoid Natural Products Herein, we report an investigation of several synthetic strategies to access the aphidicolin family of natural products. Some unsuccessful approaches include strategies featuring Diels–Alder cycloaddi...

Congratulations to Jack and Safaa on their beautiful study toward the aphidicolin family of diterpenoids that just appeared in JOC!
pubs.acs.org/doi/full/10....

UC Berkeley researchers develop ‘carbamorphine,’ a safer painkiller The molecule, coined “carbamorphine,”was built through total synthesis.

Check out this article in @dailycal.bsky.social highlighting our recently published carbamorphine work!

www.dailycal.org/news/campus/...

Check out this article highlighting our carbamorphine work!
chemistry.berkeley.edu/news/carbamo...

Congratulations to Team Carbamorphine, led by Sota, along with our collaborators from the Majumdar and McLaughlin groups on the publication of our work in PNAS!
www.pnas.org/doi/10.1073/...

What is Editing? You have not visited any articles yet, Please visit some articles to see contents here.

A brief editorial with @sarponggroup.bsky.social and @alisonwendlandt.bsky.social where we try to answer an important question: What is Editing?

pubs.acs.org/doi/full/10....

Meet Dr. Sojung Kim, Recent PhD Graduate of UC Berkeley. Headshot of Sojung with C-CAS and UC Berkeley logos

Image of Sojung in front of scientific poster. Caption: "Organic chemists synthesize molecules by connecting atoms or smaller molecule pieces together through chemical reactions. Sojung’s research focuses on using visible light (e.g., colored LED lights) as an energy source to drive new kinds of chemical reactions that ultimately enable us to build a wider variety of molecules more efficiently."

Image of Sojung skiing in Lake Tahoe. Caption: "Sojung grew up in PA and graduated from Penn State as part of the Schreyer Honors College and Millennium Scholars Program. Outside of lab, Sojung loves enjoying the CA sunshine and temperate Bay weather while exploring new restaurants in SF, beach-hopping down the Pacific Coast Highway, wine tasting in Sonoma and Napa, skiing in Lake Tahoe, and tending to her lab balcony garden."

Meet Sojung, a recent graduate of the
@sarponggroup.bsky.social!

Have a questions for Sojung? Let us know!

#NSF #Chemistry #C-CAS #Meetascientist #Chemsky

Skeletal Editing Strategies Driven by Total Synthesis ConspectusSingle-atom skeletal editing strategies that precisely modify the core frameworks of molecules have the potential to streamline and accelerate organic synthesis by enabling conceptually simp...

Congratulations to Sojung, Charis, and Logan on the publication of their Accounts of Chemical Research paper on our group's skeletal editing work, which, at its core, is inspired by total synthesis!

pubs.acs.org/doi/epdf/10....

Skeletal editing provides quick access to pharmaceutical ‘matching pairs’ Late-stage functional group switching in dibenzofurans will aid drug discovery chemistry

Check out this @chemistryworld.com highlight of Ryan and Moto's work!

www.chemistryworld.com/news/skeleta...

Chemists at @ucberkeleyofficial.bsky.social led by @sarponggroup.bsky.social figured out how to shuffle peripheral pieces of a molecule by twisting its interior structure, like rearranging a Rubik's cube. Their work, in @science.org, helps speed drug design. chemistry.berkeley.edu/news/twist-c...

Check out this article highlighting our acyl transposition work!
chemistry.berkeley.edu/news/twist-c...

1,2-Acyl transposition through photochemical skeletal rearrangement of 2,3-dihydrobenzofurans Saturated heterocycles are commonly adorned with groups that influence their biological properties. Synthetic methods that transpose existing substituents on saturated heterocycles to multiple peripheral positions are therefore highly valuable. In this ...

Congratulations to Ryan and Moto on the publication of their 1,2-acyl transposition in 2,3-dihdyrobenzofurans in @science.org!

www.science.org/doi/10.1126/...

1,2-Acyl transposition through photochemical skeletal rearrangement of 2,3-dihydrobenzofurans Saturated heterocycles are commonly adorned with groups that influence their biological properties. Synthetic methods that transpose existing substituents on saturated heterocycles to multiple periphe...

In @science.org this week, Ryan Steele and Motohiro Fujiu in @sarponggroup.bsky.social move an acyl group by transposing adjacent carbons rather than moving the oxygen 🔀

chemsky 🧪

www.science.org/doi/10.1126/...

National Academy of Sciences adds eight from UC Berkeley to its ranks - Berkeley News The new members from Berkeley have spent decades researching gene editing, materials science, very young children, the depths of the universe and more.

Check out these articles highlighting Richmond's election to the National Academy of Sciences!

news.berkeley.edu/2025/05/02/n...

chemistry.berkeley.edu/news/richmon...

National Academy of Sciences Elects Members and International Members - NAS WASHINGTON — The National Academy of Sciences announced today the election of 120 members and 30 international members in recognition of their distinguished and continuing achievements in original res...

Richmond has been elected into the US National Academy of Sciences!
www.nasonline.org/news/2025-na...

Congratulations to @gwynethpudner.bsky.social, Selena and Eric on the publication of their approach to benzannulated seven-membered rings in @synthesis1969.bsky.social!

www.thieme-connect.com/products/ejo...

Congrats to Nina for being awarded an NSF graduate research fellowship! 🎉 We are so proud of you!

Meet Suh, a graduate student in the @sarponggroup.bsky.social

Check out our instagram @nsf_ccas to learn more about Suh.

#NSF #Chemistry #C-CAS #Meetascientist

Cheminformatic Analysis of Core-Atom Transformations in Pharmaceutically Relevant Heteroaromatics Heteroaromatics are the basis for many pharmaceuticals. The ability to modify these structures through selective core-atom transformations, or “skeletal edits”, can dramatically expand the landscape f...

Congrats to Logan & our collaborators Lucas (Sigman Group) & Reilly & @charlesthechemist.bsky.social (Merck) on the publication of our work on a cheminformatic analysis of core-atom transformations in pharmaceutically relevant heteroaromatics. Check it out in J. Med. Chem. now!

tinyurl.com/42re37pd