Publications

Photoinduced Carboborative Ring Contraction Enables Regio- and Stereoselective Synthesis of Multiply Substituted Five-Membered Carbocycles and Heterocycles.

Jin, S.; Nguyen, V. T.; Dang, H. T.; Nguyen, D. P.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2017, 139, 11365–11368. (Highlighted in C&EN)

10.1021/jacs.7b07128
Transition Metal-Catalyzed C–H Functionalization of Heterocyclic N-Oxides.

Stephens, D. E.; Larionov, O. V. Top. Heterocycl. Chem. 2017, 53, 59–84.

10.1007/7081_2017_1
Assessment of Novel Curcumin Derivatives as Potent Inhibitors of Inflammation and Amyloid-β Aggregation in Alzheimer’s Disease.

Lakey-Beitia, J.; González, Y.; Doens, D.; Stephens, D. E.; Santamaría, R.;, Murillo, E.; Gutiérrez, M.; Fernández, P. L.; Rao, K. S. Larionov, O. V.; Durant-Archibold, A. A. J. Alzheimer’s Dis. 2017, DOI: 10.3233/JAD-170071.

10.3233/JAD-170071
Metal- and Additive-Free Photoinduced Borylation of Haloarenes.

Mfuh, A. M.; Schneider, B. D.; Cruces, W.; Larionov, O. V. Nat. Protoc. 2017, 12, 604–610.

10.1038/nprot.2016.184
Identification of Inhibitors of CD36-Amyloid Beta Binding as Potential Agents for Alzheimer’s Disease.

Doens, D.; Valiente, P. A.; Mfuh, A. M.; Vo, A. X. T.; Tristan, A.; Carreño, L.; Quijada, M.; Nguyen, V. T.; Perry, G.; Larionov, O. V.; Lleonart, R.; Fernández, P. L. ACS Chem. Neurosci. 2017, 10.1021/acschemneuro.6b00386.

10.1021/acschemneuro.6b00386
Cytotoxicity and Mechanism of Action of the Marine-Derived Fungal Metabolite Trichodermamide B and Synthetic Analogues.

Jans, P. E.; Mfuh, A. M.; Arman, H. D.; Shaffer, C. V.; Larionov, O. V.; Mooberry, S. L. J. Nat. Prod. 2017, 80, 676–683.

10.1021/acs.jnatprod.6b00963
Organocatalytic Synthesis of Methylene-Bridged N-Heterobiaryls.

Stephens, D. E.; Nguyen, V. T.; Chhetri, B.; Clark, E. R.; Arman, H. D.; Larionov, O. V. Org. Lett. 2016, 18, 5808–5811.

10.1021/acs.orglett.6b02719
Mechanistic Insights into the Potassium tert-Butoxide-Mediated Synthesis of N-Heterobiaryls.

Stephens, D. E.; Lakey-Beitia, J.; Burch, J. E.; Arman, H. D.; Larionov, O. V. Chem. Commun. 2016, 52, 9945–9948.

10.1039/C6CC04816A
Additive- and Metal-Free, Predictably 1,2- and 1,3-Regioselective, Photoinduced Dual C–H/C–X Borylation of Haloarenes.

Mfuh, A. M.; Nguyen, V. T.; Chhetri, B.; Burch, J. E.; Doyle, J. D.; Nesterov, V. N.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2016, 138, 8408–8411.

10.1021/jacs.6b05436
Insights into the Structural Patterns of the Antileishmanial Activity of Bi- and Tricyclic N-Heterocycles.

Herrera, L.; Stephens, D. E.; D’Avila, A.; George, K. A.; Arman, H. D.; Zhang, Y.; Perry, G.; Lleonart, R.; Larionov, O. V.; Fernández, P. L. Org. Biomol. Chem. 2016, 14, 7053–7060.

10.1039/C6OB01149G
Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts.

Mfuh, A. M.; Doyle, J. D.; Chhetri, B.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2016, 139, 2985–2988.

10.1021/jacs.6b01376
Recent Advances in the C–H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Stephens, D. E.; Larionov, O. V. Tetrahedron 2015, 71, 8683–8716.

10.1016/j.tet.2015.08.034
Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core. Mfuh, A. M.; Zhang, Y.; Stephens, D. E.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2015, 137, 8050–8053. 10.1021/jacs.5b05205
  Heterocyclic N-Oxides – An Emerging Class of Therapeutic Agents.

Mfuh, A. M.; Larionov, O. V. Curr. Med. Chem. 2015, 22, 2819–2857.

10.2174/0929867322666150619104007
  Experimental and Mechanistic Analysis of the Palladium-Catalyzed Oxidative C8-Selective C–H Homocoupling of Quinoline N-Oxides. Stephens, D. E.; Lakey-Beitia, J.; Chavez, G.; Ilie, C.; Arman, H. D.; Larionov, O. V. Chem. Comm. 2015, 51, 9507–9510. 10.1039/c5cc02227d
  Palladium-Catalyzed C8-Selective C–H Arylation of Quinoline N-Oxides: Insights into the Electronic, Steric and Solvation Effects on the Site-Selectivity by Mechanistic and DFT Computational Studies. Stephens, D. E.; Lakey-Beitia, J.; Atesin, A. C.; Ateşin, T. A.; Chavez, G.; Arman, H. D.; Larionov, O. V. ACS Catal. 2015, 5, 167−175. 10.1021/cs501813v
  Synthetic and Mechanistic Aspects of the Regioselective Base-Mediated Reaction of Perfluoroalkyl- and Perfluoroarylsilanes with Heterocyclic N-Oxides. Stephens, D. E.; Chavez, G.; Valdes, M.; Dovalina, M.; Arman, H. D.; Larionov, O. V. Org. Biomol. Chem. 2014, 12, 6190-6199. 10.1039/C4OB01088D
  Straightforward Access to Hexahydropyrrolo[2,3-b]indole Core by a Regioselective C3-Azo Coupling Reaction of Arenediazonium Compounds with Tryptamines. Stephens, D. E.; Larionov, O. V. Eur. J. Org. Chem. 2014, 3662–3670. 10.1002/ejoc.201402088
  Coupling of deoxyribonucleic acid to solid supports using 3′ terminal ribose incorporation. Jia, Y.; Larionov, O.; Jarrett, H. W. J. Chromatogr. A 2014, 1339, 73–79. 10.1002/ejoc.201402088
  Insights into the Mechanistic and Synthetic Aspects of the Mo/P-Catalyzed Oxidation of N-Heterocycles. Larionov, O. V.; Stephens, D.; Chavez, G.; Mfuh, A.; Hadi, A.; Naumova, A.; Skenderi, B. Org. Biomol. Chem. 2014, 12, 3026–3036. 10.1039/C4OB00115J
  Direct, Catalytic, and Regioselective Synthesis of 2-Alkyl-, Aryl-, and Alkenyl-Substituted N-Heterocycles from N-Oxides. Larionov, O. V.; Stephens, D.; Mfuh, A.; Chavez, G. Org. Lett. 2014, 16, 864–867. ol403631k  
  Three-component reaction of small-ring cyclic amines with arynes and acetonitrile. Stephens, D.; Zhang, Y.; Cormier, M.; Chavez, G.; Arman, H.; Larionov, O. V. Chem. Comm. 2013, 49, 6558–6560. c3cc42854k
  Catalytic Diastereo- and Enantioselective Annulations between Transient Nitrosoalkenes and Indoles. Zhang, Y.; Stephens, D.; Hernandez, G.; Mendoza, R.; Larionov, O. V. Chem. Eur. J. 2012, 18, 16612–16615. chem.201203435
  Synthesis and Biological Activity of Simplified Belactosin C Analogues. de Meijere, A.; Korotkov, V. S.; Lygin, A. V.; Larionov, O. V.; Sokolov, V. V.; Graef, T.; Es-Sayed, M. Org. Biomol. Chem. 2012, 10, 6363-6374.
  Synthesis and Biological Activity of Optimized Belactosin C Congeners. Korotkov, V. S.; Ludwig, A.; Larionov, O. V.; Lygin, A. V.; Groll, M.; de Meijere, A. Org. Biomol. Chem. 2011, 9, 7791–7798.
  Ni(II)-Catalyzed Enantioselective Conjugate Addition of Acetylenes to α,β-Enones. Larionov, O. V.; Corey, E. J. Org. Lett. 2010, 12, 300–302.
  Total Synthesis and Biological Evaluation of Amphidinolide V and Analogues. Fürstner, A.; Flügge, S.; Larionov, O.; Takahashi, Y.; Kubota, T.; Kobayashi, J. Chem. Eur. J. 2009, 15, 4011–4029.
  The Effect of New Proteasome Inhibitors, Belactosin A and C, on Protein Metabolism in Isolated Rat Skeletal Muscle. Muthny, T.: Kovarik, M.; Sispera, L.; de Meijere, A.; Larionov, O. V., Tilser, I.; Holecek, M. J. Physiol. Biochem. 2009, 65, 137–146.
  An Unconventional Approach to the Enantioselective Synthesis of Caryophylloids. Larionov, O. V.; Corey, E. J. J. Am. Chem. Soc. 2008, 130, 2954-2955.
  GaCl3-Catalyzed Insertion of Diazene Derivatives into the Cyclopropane Ring. Korotkov, V. I.; Larionov, O. V.; de Meijere, A. J. Org. Chem. 2007, 72, 7504–7510.
  What is Amphidinolide V? Report on a Likely Conquest. Fürstner, A.; Larionov, O.; Flügge, S. Angew. Chem. 2007, 119, 5641–5644; Angew. Chem. Int. Ed. 2007, 46, 5545–5548.
  Diastereoselective Synthesis of trans-2-Substituted Cyclopropylamines. Tanguy, C.; Bertus, P.; Szymoniak, J.; Larionov, O. V.; de Meijere, A. Synlett 2006, 18, 3164–3166.
  Convenient Access to 2-Arylpyrroles from 2-Lithio-N,N-dibenzylcyclopropylamine and Nitriles. Tanguy, C.; Bertus, P.; Szymoniak, J.; Larionov, O. V.; de Meijere, A. Synlett 2006, 14, 2339–2341.
  Practical Syntheses of Both Enantiomers of Cyclopropylglycine and of Methyl 2-Cyclopropyl-2-(N-Boc-imino)acetate. Larionov, O. V.; de Meijere, A. Adv. Synth. Cat. 2006, 348, 1071–1078.
  Ln(OTf)3-Catalyzed Insertion of Aryl Isocyanides into the Cyclopropane Ring. Korotkov V. S.; Larionov, O. V.; de Meijere, A. Synthesis 2006, 21, 3542–3546.
  Novel Inhibitor Binding Mode of Homobelactosin C to Proteasomes: New Insights into Class I MHC Ligand Generation. Groll, M.; Larionov, O. V.; de Meijere, A.; Huber, R. Proc. Natl. Acad. Sci. USA (PNAS) 2006, 103, 4576–4579.
  Asymmetric Synthesis of 3-(trans-2-Nitrocyclopropyl)alanine and 3-(trans-2-aminocyclopropyl)alanine. de Meijere, A.; Larionov, O. V. in Asymmetric Synthesis – The Essentials. Ed. Bräse, S.; Christmann, M. Wiley-VCH, 2006.
  Versatile Direct Synthesis of Oligosubstituted Pyrroles by Cycloaddition of α-Metallated Isocyanides to Acetylenes. Larionov, O. V.; de Meijere, A. Angew. Chem. 2005, 117, 5809–5813; Angew. Chem. Int. Ed. 2005, 44, 5664–5667.
  Facile Preparation of tert-Butyl 1-tert-Butoxycarbonylaminocyclopent-3-enecarboxylate from Inexpensive Starting Materials. Larionov, O. V.; Kozhushkov, S. I.; de Meijere, A. Synthesis 2005, 1, 158–160.
  Total Syntheses of Belactosin A, Belactosin C and the Homoanalogue. Larionov, O. V.; de Meijere, A. Org. Lett. 2004, 6, 2153–2156.
  (1′S,2R,3S,4S)-Ethyl-2-hydroxy-4-methyl-3-(1′-phenylethylcarbamoyl)hexanoate. Larionov, O. V.; de Meijere, A.; Yufit, D. S.; Howard, J. A. K. Acta Crystallogr. E 2004, 60, O681–O683.
  Rational Synthesis of All Four Stereoisomers of 3-(trans-2-Aminocyclopropyl)alanine. Larionov, O. V.; Kozhushkov, S. I.; Brandl, M.; de Meijere, A. Mendeleev Comm. 2003, 5, 199–200.
  Synthesis of α-Amino Acids via Asymmetric PTC Alkylation of Achiral Ni(II) Complexes of Glycine-derived Schiff Bases. Belokon, Y. N.; Bespalova, N. B.; Churkina, T. D.; Cisarova I.; Ezernitskaya, M. G.; Harutyunyan, S. R.; Hrdina, R.; Kagan, H. B.; Kocovsky, P.; Kochetkov, K. A.; Larionov, O. V.; Lyssenko, K. A.; North, M.; Polasek, M.; Peregudov, A. S.; Prisyazhnyuk, V. V.; Vyskocil, S. J. Am. Chem. Soc. 2003, 125, 12860–12871.
  New Protocol for Efficient N-Chlorinations of Amides and Carbamates. Larionov, O. V.; Kozhushkov, S. I.; de Meijere, A. Synthesis 2003, 12, 1916–1919.
  Photoelectron Spectra and Electronic Structures of Some Acceptor-substituted Cyclopropanes: Linear Correlation of Substituent Effects on MO Energies with Molecular Structures. Rademacher, P.; Coskun, T.; Kowski, K.; Larionov, O.; de Meijere, A. Chem. Eur. J. 2003, 9, 2953–2962.
  Productive Asymmetric Synthesis of All Four Diastereomers of 3-(trans-2-Nitrocyclopropyl)alanine from Glycine with (S)- or (R)-2-[(N-Benzylprolyl)amino]benzophenone as a Reusable Chiral Auxiliary. Larionov, O. V.; Savel’eva, T. F.; Kochetkov, K. A.; Ikonnikov, N. S.; Kozhushkov, S. I.; Yufit, D. S.; Howard, J. A. K.; Khrustalev, V. N.; Belokon, Y. N.; de Meijere, A. Eur. J. Org. Chem. 2003, 869–877.
  Highly Efficient Phase Transfer Catalytic Synthesis of α-Amino Acids Based on a Novel Catalyst/Substrate Pair. Belokon’, Yu. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Larionov, O. V.; Harutyunyan, S. I.; Vyskočil, S.; North, M., and Kagan, H. B. Angew. Chem. Int. Edit. 2001, 40, 1948–1951.
  Asymmetric PTC C-Alkylation Catalyzed by Chiral Derivatives of Tartaric Acid and Aminophenols. Synthesis of (R)- and (S)-α-Methyl Amino Acids. Belokon’, Yu. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Singh, I.; Parmar, V. S.; Vyskočil, S., and Kagan, H. B. J. Org. Chem. 2000 65, 7041–7048.
  Asymmetric Alkylation Catalyzed by Chiral Alkali Metal Alkoxides of TADDOL. Synthesis of α-Amino Acids. Belokon’, Yu. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V., and Kagan, H. B. Russ. Chem. Bull. 2000, 49, 1395–1398.
  Synthesis and Photochemical Properties of Diimine Propane-1,3-dithiolate Pt(II) Complexes. Larionov, O. V.; Zheligovskaya, N. N.; Vainstein, Yu. A.; Melnikov, M. Ya. Russ. J. Coord. Chem. 1999, 25, 271–275.
  Asymmetric PTC C-Alkylation Mediated by TADDOL – Novel Route to Enantiomerically Enriched α-Alkyl-α-Amino Acids. Belokon’, Yu. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S., Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R., and Kagan, H. B. Tetrahedron: Asymmetry, 1998, 9, 851–857.