Research
The research interest of the Piersanti's group is synthetic organic chemistry in broad terms, including natural product synthesis (mainly indole-based) in concert with the discovery and the development of new transformations for organic synthesis including catalytic and asymmetric processes (mainly exploiting two-carbon nitrogen-containing electrophiles).
Since 2017, he is involved in the field of (bio)molecules with redox-active sulfhydryl function(s) (thiol compounds) chemicals research, as co-founder of GLUOS srl a Spin off at University of Urbino. http://www.gluos.it/
Selected pubblication
- Pecchini P, Fochi M., Bartoccini F., Piersanti G., Bernardi L. Enantioselective organocatalytic strategies to noncanonical α‐amino acids Chemical Science 2024, LINK
Retini M, Sisti A, Olivieri D, Mari M, Bartoccini F, Piersanti G. Practical and Selective Syntheses of S-Acyl and N-Acyl Glutathiones with N-Acyl Imidazoles in Water European Journal of Organic Chemistry 2024, LINK
Leoni G, Bartoccini F, Piersanti G. General Access to Clavine Alkaloids via a Rhodium(I)-Catalyzed Diastereoselective Hayashi-Miyaura Reaction Advanced Synthesis & Catalysis 2024, 366, 6, 1397-1404. LINK
Diotallevi F, Bartoccini F, Piersanti G. A Short Synthesis of (−)-6,7-Secoagroclavine via Metal-Free Reductive Coupling European Journal of Organic Chemistry, 2024, LINK
Regni A, Bartoccini F, Piersanti G. Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine Beilstein Journal of Organic Chemistry 2023, 19, 918-927. Open Access https://doi.org/10.3762/bjoc.19.70
Bartolucci S, Retini M, Fanini F, Paderni D, Piersanti G. Synthesis and Fluorescence Properties of 4-Cyano and 4-Formyl Melatonin as Putative Melatoninergic Ligands. ACS Omega 2023, 8, 24, 22190–22194. Open Access https://pubs.acs.org/doi/10.1021/acsomega.3c02518
Fraternale A,..., Bartoccini F, Retini M, Piersanti G. et al Targeting SARS‐CoV‐2 by synthetic dual‐acting thiol compounds that inhibit Spike/ACE2 interaction and viral protein production. The FASEB Journal. 2023; 37, e22741. Open Access https://doi.org/10.1096/fj.202201157RR
One of the most downloaded (within 10%) during its first 12 months from pubblication
Retini M, Bartolucci S, Bartoccini F, Piersanti G. Asymmetric Alkylation of Cyclic Ketones with Dehydroalanine via H‐Bond‐Directing Enamine Catalysis: Straightforward Access to Enantiopure Unnatural α‐Amino Acids. Chem. Eur. J. 2022, 28, e202201994 Open Access https://doi.org/10.1002/chem.202201994
Selected as Hot Topics of organocatalysis in Wiley Journals SYNFACTS HIGHLIGHT Featured in Org. Chem. Highlights
Bartoccini F, Retini M, Crinelli R, Menotta M, Fraternale A, Piersanti G. Dithiol Based on L-Cysteine and Cysteamine as a Disulfide-Reducing Agent. J. Org. Chem. 2022, 87 (15), 10073–10079. Open Access https://doi.org/10.1021/acs.joc.2c01050.
Bartoccini F, Regni A, Retini M, Piersanti G. Asymmetric Total Synthesis of All Rugulovasine Stereoisomers and Preliminary Evaluation of Their Biological Properties. European Journal of Organic Chemistry 2022 (17), e202200315. Open Access https://doi.org/10.1002/ejoc.202200315
Highlighted in ChemistryViews
Bartoccini F, Regni A, Retini M, Piersanti G. Concise catalytic asymmetric synthesis of (R)-4-amino Uhle's ketone. Organic & Biomolecular Chemistry, 2021, 19, 2932-2940. DOI: 10.1039/D1OB00353D
Bartoccini F, Piersanti G. Synthesis and Reactivity of Uhle’s Ketone and Its Derivatives. Synthesis, 2021, 53, 1396-1408. https://doi.org/10.1055/a-1340-3423.
Retini M, Bartoccini F, Zappia G, Piersanti G. Novel, Chiral, and Enantiopure C 2 ‐Symmetric Thioureas Promote Asymmetric Protio‐Pictet‐Spengler Reactions by Anion‐Binding Catalysis. European Journal of Organic Chemistry, 2021, 825-829. DOI: 10.1002/ejoc.202001501
Bartoccini F, Fanini F, Retini M, Piersanti G. General synthesis of unnatural 4-, 5-, 6-, and 7-bromo-D-tryptophans by means of a regioselective indole alkylation. Tetrahedron Letters, 2020, 151923. https://doi.org/10.1016/j.tetlet.2020.151923
Bartoccini F, Retini M, Piersanti G. C3-Alkylation of indoles and oxindoles by alcohols by means of borrowing hydrogen methodology. Tetrahedron Letters, 2020, 151875. https://doi.org/10.1016/j.tetlet.2020.151875
Bartoccini F, Mari M, Retini M, Galarini R, Bartolucci S, Piersanti G. Single‐Step Synthesis of Dehydroalanine Derivatives via a Brønsted Acid‐Catalyzed Multicomponent Reaction. ChemistrySelect 2020, 5, 3330-3336. https://doi.org/10.1002/slct.202000898
Bartoccini F, Retini M, Piersanti G. et al Identification of a 2, 4-diaminopyrimidine scaffold targeting Trypanosoma brucei pteridine reductase 1 from the LIBRA compound library screening campaign. European Journal of Medicinal Chemistry 2020, 189, 112047. https://doi.org/10.1016/j.ejmech.2020.112047
Bartoccini F, Venturi S, Retini M, Mari M, Piersanti G. Total Synthesis of (-)-Clavicipitic Acid via γ, γ-Dimethylallyltryptophan (DMAT) and Chemoselective C− H Hydroxylation. J. Org. Chem. 2019, 84, 8027−8034. https://doi.org/10.1021/acs.joc.9b00879
Bartoccini F, Mari M, Retini M, Bartolucci S, Piersanti G. Organocatalytic Aza-Friedel–Crafts/Lactonization Domino Reaction of Naphthols and Phenols with 2-Acetamidoacrylate to Naphtho- and Benzofuranones Bearing a Quaternary Center at the C3 Positio. J. Org. Chem. 2018, 83 (19), 12275-12283. https://doi.org/10.1021/acs.joc.8b01774
Di Gregorio G, Mari M, Bartoccini F, Piersanti G. Iron-Catalyzed Direct C3-Benzylation of Indoles with Benzyl Alcohols through Borrowing Hydrogen. J. Org. Chem. 2017, 82 (16), 8769-8775. https://doi.org/10.1021/acs.joc.7b01603
Bartoccini F, Cannas DM, Fini F, Piersanti G. Palladium(II)-Catalyzed Cross-Dehydrogenative Coupling (CDC) of N-Phthaloyl Dehydroalanine Esters with Simple Arenes: Stereoselective Synthesis of Z-Dehydrophenylalanine Derivative. Org. Lett. 2016, 18 (11), 2762-2765. https://doi.org/10.1021/acs.orglett.6b01255
Bartolucci S, Mari M, Bedini A, Piersanti G, Spadoni G. Iridium-Catalyzed Direct Synthesis of Tryptamine Derivatives from Indoles: Exploiting N-Protected beta-Amino Alcohols as Alkylating Agents. J. Org. Chem. 2015, 80 (6), 3217–3222. https://doi.org/10.1021/acs.joc.5b00195
Bartoccini F, Casoli M, Mari M, Piersanti G. Synthesis of (+/-)-cis-Clavicipitic Acid by a Rh (I)-Catalyzed Intramolecular Imine Hydroarylation Reaction. J. Org. Chem. 2014, 79 (7), 3255–3259. https://doi.org/10.1021/jo500245s
Mari M, Bartoccini F, Piersanti G. Synthesis of (−)-Epi-Indolactam V by an Intramolecular Buchwald–Hartwig C–N Coupling Cyclization Reaction. J. Org. Chem. 2013, 78 (15), 7727-7734 . https://doi.org/10.1021/jo4013767
Bartolucci S, Bartoccini F, Righi M, Piersanti G. Direct, Regioselective, and Chemoselective Preparation of Novel Boronated Tryptophans by Friedel–Crafts Alkylation. Org. Lett. 2012,14 (2), 600–603. https://doi.org/10.1021/ol203216h
Righi M, Bartoccini F, Lucarini S, Piersanti G Organocatalytic synthesis of α- quaternary amino acid derivatives via aza-Friedel–Crafts alkylation of indoles with simple α- amidoacrylates Tetrahedron 2011, 67 (41), 7923-7928. https://doi.org/10.1016/j.tet.2011.08.039
Lucarini S, Bartoccini F, Battistoni F, Diamanmtini G, Piersanti G., Righi M, Spadoni G . A Novel One-Pot Approach Of Hexahydropyrrolo[2,3-b]Indole Nucleus By A Cascade Addition/Cyclization Strategy: Synthesis Of (±)-Esermethole. Org. Lett. 2010, 12 (17), 3844-3847. https://doi.org/10.1021/ol101527j
Piersanti G, Remi F, Fusi V, Formica M, Giorgi L, Zappia G. Direct Preparation of Unsymmetrical Difunctionalized Cyclen Derivatives by an Ugi Multicomponent Reaction. Org. Lett. 2009, 11 (2), 417-420. https://doi.org/10.1021/ol802674r
Angelini E, Balsamini C, Bartoccini F, Lucarini S, Piersanti G. Switchable reactivity of acylated alpha, beta-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid. J. Org. Chem. 2008, 73 (14), 5654-5657. https://doi.org/10.1021/jo800881u
Patents
Bartoccini F, Mari M, Retini M, Piersanti G. Initial patent application (number: 102021000019529; Priority date: 22/07/2021).
Bartoccini F, Fraternale A, Piersanti G. Method for the synthesis of glutathione derivatives. WO 2019102397, 2019. Espacenet
Cabri W, Minetti P, Piersanti G, Tarzia G. WO2010106145 (A1), 2010 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Espacenet
Tarzia G, Piersanti G, Minetti P, Di Cesare MA, Gallo G, Giorgi F, Giorgi L. WO 2003011864 (A1), 2003 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Espacenet