Sarpong, Richmond - University of California, Berkeley

个人简介

Born 1974 B.A. (Chemistry) Macalester College (1995) Ph.D. Organic Chemistry, Princeton University (2001) UNCF-Pfizer Postdoctoral Fellow, Caltech, 2000-2004

研究领域

Organic and Organometallic Chemistry — Total synthesis of biologically active and architecturally complex natural products as a platform for the development of new synthetic methods and strategies. Central to our research interests is the total synthesis of natural products with a keen eye toward the development of new synthetic methods and strategies. In concert with this general program, we look to nature to inspire our choice of synthetic targets (natural products) and some of our strategies (e.g., bio-mimetic approaches) to natural product synthesis. The compounds that we synthesize in our laboratory may ultimately become important as tools to study biological systems or provide a starting point for the development of therapeutics. The challenge of a total synthesis provides a unique opportunity to test the limits of synthetic methodology and to invent new reactions. The formation of carbon-carbon bonds (C-C bonds) is of fundamental importance to synthetic organic chemistry. Our group seeks to address some of the current limitations in synthetic organic chemistry by defining new directions for C-C bond formation and then validating our methodology in the arena of complex molecule synthesis. In this regard, we are interested in (A) C-C bond forming processes that are coupled with the energetically 'downhill' events of strain release and aromatization to provide new strategies to access natural product motifs, (B) the generation of metal vinylidenes under mild reaction conditions as a new entry into C-H functionalization and (C) novel access to reactive intermediates such as metallo-carbenoids and radicals. Ultimately, we anticipate that our interests will evolve, depending on a student's interest or fascinating new transformations that we encounter. Among the natural products currently of interest in our group are the teleocidin B family of indole alkaloids (potent protein kinase C tumor promoters), the cyathane diterpenoids scabronine A and erinacine E (active stimulants of nerve growth factor biosynthesis) and the trichothecane sesquiterpenoids verrucarin A and satratoxin H which are mycotoxins that also possess cytotoxic properties.

近期论文

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Tetrahedron Lett. 2022, Accepted. Synthesis of substituted benzoates using a rhodium-mediated Hopf cyclization of 1,3-dien-5-ynes accessed from 2-pyrones Gardner, K. E.; Sarpong, R. J. Am. Chem. Soc. 2022, Accepted. Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion Bartholomew, G. L.; Carpaneto, F.; Sarpong, R. J. Am. Chem. Soc. 2022, Accepted. General Synthetic Approach to Diverse Taxane Cores Perea, M. A.†; Wang, B.†; Wyler, B. C.; Ham, J. S.; O’Connor, N. R.; Nagasawa, S.; Kimura, Y.; Manske, C.; Scherübl, M.; Nguyen, J. M.; Sarpong, R. J. Am. Chem. Soc. 2022, Accepted. Development of a C−C Bond Cleavage/Vinylation/Mizoroki−Heck Cascade Reaction: Application to the Total Synthesis of 14- and 15- Hydroxypatchoulol Na, C. G.; Kang, S. H.; Sarpong, R. J. Am. Chem. Soc. 2022, Accepted. Unified Total Syntheses of Benzenoid Cephalotane-Type Norditerpenoids: Cephanolides and Ceforalides Sennari, G.; Gardner, K. E.†; Wiesler, S.†; Haider, M.; Eggert, A.; Sarpong, R. J. Am. Chem. Soc. 2022, 144, 17277–17294. Strategy Evolution in a Skeletal Remodeling and C–H Functionalization-Based Synthesis of the Longiborneol Sesquiterpenoids Lusi, R. F.†; Sennari, G.†; Sarpong, R. Nat. Synth. 2022, 1, 352–364. Single-atom logic for heterocycle editing Jurczyk, J.; Woo, J. Kim, S. F.; Dherange, B. D.; Sarpong, R.; Levin, M. D. Acc. Chem. Res. 2022, 55, 746–758.C–C Bond Cleavage of α-Pinene Derivatives Prepared from Carvone as a General Strategy for Complex Molecule Synthesis Lusi, R. F†; Perea, M. A.†; Sarpong, R. Nat. Chem. 2022, 14, 450–456. (Previously ChemRxiv.)Total synthesis of nine longiborneol sesquiterpenoids using a functionalized camphor strategy Lusi, R. F†; Sennari, G.†; Sarpong, R. Tetrahedron 2021, 104, 132584. Strategic elements in computer-assisted retrosynthesis: A case studyof the pupukeanane natural products Hardy, M. H.; Nan, B.; Wiest, O.; Sarpong, R. J. Am. Chem. Soc. 2021, 143, 20482–20490. Rearrangements of the Chrysanthenol Core: Application to a Formal Synthesis of Xishacorene B Jones, K. E.; Park, B.; Doering, N. A.; Baik, M.-H.; Sarpong, R. Chem. Rev. 2021, 122, 10126–10169. Site-Selective Cross-Coupling of Polyhalogenated Arenes and Heteroarenes with Identical Halogen Groups Palani, V.†; Perea, M. A.†; Sarpong, R. J. Org. Chem. 2021, 86, 12436–12442. Sequential Norrish–Yang Cyclization and C–C Cleavage/Cross-Coupling of a [4.1.0] Fused Saturated Azacycle Roberts, C. A.; Park, B.; Xu, L.-P.; Roque, J. B.; Yeung, C. S.; Musaev, D. G.; Sarpong, R.; LaLonde, R. L. Science 2021, 373, 1004–1012. Photo-mediated ring contraction of saturated heterocycles Jurczyk, J.; Lux, M. C.; Adpressa, D.; Kim, S. F.; Lam, Y.; Yeung, C. S.; Sarpong, R. Nat. Rev. Methods Primers 2021, 1, 43.C–H activation Rogge, T.; Kaplaneris, N.; Chatani, N.; Kim, J.; Chang, S.; Punji, B.; Schafer, L. L.; Musaev, D. G.; Wencel-Delord, J.; Roberts, C. A.; Sarpong, R.; Wilson, Z. E.; Brimble, M. A.; Johansson, M. J.; Ackermann, L. Top. Catal. 2022, 65, 418–432. Computational Study of Key Mechanistic Details for a Proposed Copper (I)-Mediated Deconstructive Fluorination of N-Protected Cyclic Amines Kaledin, A. L.; Roque, J. B.; Sarpong, R.; Musaev, D. G. Nat. Rev. Methods Primers 2021, 1, 23. Automation and computer-assisted planning for chemical synthesis Shen, Y.†; Borowski, J. E.†; Hardy, M. A.†; Sarpong, R.; Doyle, A. G.; Cernak, T. J. Am. Chem. Soc. 2021, 143, 4732–4740. (PMCID: 8017526) Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids Haley, H. M. S.†; Payer, S. E.†; Papidocha, S. M.; Clemens, S.; Nyenhuis, J.; Sarpong, R. J. Am. Chem. Soc. 2021, 143, 3889–3900. Key Mechanistic Features of the Silver(I)-Mediated Deconstructive Fluorination of Cyclic Amines: Multistate Reactivity versus Single-Electron Transfer Roque, J. B.; Sarpong, R.; Musaev, D. G. J. Am. Chem. Soc. 2021, 143, 2710–2715. Total synthesis of the Cephalotaxus Norditerpenoids (±)-Cephanolides A–D Haider, M.†; Sennari, G.†; Eggert, A.; Sarpong, R.