Scientific Papers
Contacting the PI
Joseph P. KonopelskiUniversity of California, Santa Cruz
Dept. of Chemistry & Biochemistry
1156 High St.
Santa Cruz, CA 95064
Office: PSB 344
Phone: 831.459.4676
Email: joek@chemistry.ucsc.edu
Contacting the Lab
Grad Student Office / Lab: PSB 379Phone: 831.459.4669
Present - 2000
Gerstenberger, B.S.; Lin, J.; Mimieux, Y.S.; Brown, L.E.; Oliver, A.G.; Konopelski, J.P. "Structural characterization of an enantiomerically pure amino acid imidazolide and direct formation of the β-lactam nucleus from an α-amino acid" Organic Letters, 2008, 10, 369-372.
Xia, J.; Brown, L.E.; Konopelski, J.P. "Welwistatin support studies: Expansion and limitation of aryllead (IV) coupling reactions" Journal of Organic Chemistry, 2007, 72, 6885-6890.
White, K.N.; Sen, I.; Szundi, I.; Landaverry, Y.R.; Bria, L.E.; Konopelski, J.P.; Olmstead, M.M.; Einarsdottir, O. "Synthesis and structural characterization of cross-linked histidine-phenol Cu(II) complexes as cytochrome c oxidase active site models" Chemical Communications, 2007, 3252-3254.
Landaverry, Y.R.; White, K.N.; Olmstead, M.M.; Einarsdottir, O.; Konopelski, J.P. "Cytochrome C oxidase active site mimics: New ligands for copper and an unexpected oxidative C-C bond formation" Heterocycles, 2006, 70, 147-152.
Chen, W.; Davies, J.R.; Ghosh, D.; Tong, M.C.; Konopelski, J.P.; Chen, S.W. "Carbene-functionalized ruthenium nanoparticles" Chemistry of Materials, 2006, 18, 5253-5259.
White, K.N.; Konopelski, J.P. "Facile synthesis of highly functionalized N-methyl amino acid esters without side-chain protection" Organic Letters, 2005, 7, 4111-4112.
Gerstenberger, B.S.; Konopelski, J.P. "tert-Butyldiphenylsilylethyl (TBDPSE): A practical protecting group of phenols" Journal of Organic Chemistry, 2005, 70, 1467-1470.
Konopelski, J.P.; Lin, J.Z.; Wenzel, P.J.; Deng, H.B.; Elliot, G.I.; Gerstenberger, B.S. "Carbanion stabilization by distal silyloxy groups. Origin of the high diastereoselectivity in the formation of quaternary centers with aryllead (IV) triacetate reagents" Organic Letters, 2002, 4, 4121-4124.
Busque, F.; Hopkins, S.A.; Konopelski, J.P. "Progress toward a peptidomimetic of laminin-derived pentapeptide YIGSR: Synthesis of the unique tricyclic core structure" Journal of Organic Chemistry, 2002, 67, 6097-6103.
Cappuccio, J.A.; Ayala, I.; Elliott, G.I.; Szundi, I.; Lewis, J.; Konopelski, J.P.; Barry, B.A.; Einarsdottir, O. "Modeling the active site of cytochrome oxidase: synthesis and characterization of a cross-linked histidine-phenol" Journal of the American Chemical Society, 2002, 124, 1750-1760.
Deng, H.B.; Konopelski, J.P. "Aryllead (IV) reagents in synthesis: Formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate" Organic Letters, 2001, 3, 3001-3004.
Elliott, G.I.; Konopelski, J.P. "Arylation with organolead and organobismuth reagents" Tetrahedron, 2001, 57, 5683-5705.
Hopkins, S.A.; Konopelski, J.P.; Olmstead, M.M.; Banks, H.D. "Conformational analysis of peptides containing enantiomerically pure α-methylasparagine: Correspondence between computed and solid state structures" Tetrahedron, 2000, 56, 9733-9737.
Elliott, G.I.; Konopelski, J.P. "Complete N-1 regiocontrol in the formation of N-arylimidazoles. Synthesis of the active site His-Tyr side chain coupled dipeptide of cytochrome C oxidase" Organic Letters, 2000, 2, 3055-3057.
1999 - 1990
Elliott, G.I.; Konopelski, J.P.; Olmstead, M.M. "Diastereoselectivity in the formation of quaternary centers with aryllead (IV) tricarboxylates" Organic Letters, 1999, 1, 1867-1870.
Hopkins, S.A.; Ritsema, T.A.; Konopelski, J.P. "Enantiomerically pure tetrahydropyrimidinones in asymmetric synthesis: Preparation of a protected α-methylasparagine derivative and corresponding dipeptides" Journal of Organic Chemistry, 1999, 64, 7885-7889.
Konopelski, J.P.; Wei, Y.Y.; Olmstead, M.M. "Dipeptide surrogates containing asparagine-derived tetrahydropyrimidinones: Structure and amide rotamer stereochemistry of a proline mimic" Journal of Organic Chemistry, 1999, 64, 5148-5151.
Hang, H.C.; Drotleff, E.; Elliott, G.I.; Ritsema, T.A.; Konopelski, J.P. "The synthesis of 3-methoxycarbonylbenzofuran-2(3H)-one derivatives via copper (I) catalyzed coupling of o-bromophenols with dimethyl malonate" Synthesis, 1999, 3, 398-400.
Konopelski, J.P.; Deng, H.B.; Schiemann, K.; Keane, J.M.; Olmstead, M.M. "Stereoselective conjugate addition directed by an enantiomerically pure ketal. Preparation of the cyclohexanone fragment of N-methylwelwitindolinone C isothiocyanate" Synlett, 1998, 10, 1105.
Konopelski, J.P.; Filonova, L.K.; Olmstead, M.M. "Dipeptide surrogates containing asparagine-derived tetrahydropyrimidinones: Preparation, structure, and use in solid phase synthesis" Journal of the American Chemical Society, 1997, 119, 4305-4306.
Konopelski, J.P.; Hottenroth, J.M.; Oltra, H.M.; Veliz, E.A.; Yang, Z.C. "Synthetic studies on diazonamide A. Benzofuranone-tyrosine and indole-oxazole fragment support studies" Synlett, 1996, 7, 609.
Lakner, F.J.; Chu, K.S.; Negrete, G.R.; Konopelski, J.P. "Synthesis of enantiomerically pure beta-amino acids from 2-tert-butyl-1-carbomethoxy-2,-dihydro-4(1H)-pyrimidinone: (R)-3-amino-3-(p-methoxyphenyl) -propionic acid-(1(2H)-pyrimidinecarboxylic acid, 2-(1,1-dimethylethyl)-3,4-dihydro-4-oxo-methyl ester, (R)- or (S)-)" Organic Syntheses, 1996, 73, 201-214.
Sanchez, A.J.; Konopelski, J.P. "Phenol benzylic epoxide to quinone methide electron reorganization - Synthesis of (+/-)-taxodone" Journal of Organic Chemistry, 1994, 59, 5445-5452.
Sanchez, A.J.; Konopelski, J.P. "The first synthesis of (+/-)-taxodone" Synlett, 1994, 5, 335-336.
Chu, K.S.; Konopelski, J.P. "Self-reproduction of chirality - Asymmetric synthesis of β-alkyl-β-amino acids from enantiomerically pure dihydropyrimidinones" Tetrahedron, 1993, 49, 9183-9190.
Konopelski, J.P.; Kasar, R.A. "Synthesis and reactions of achiral 3-substituted vinylketene acetals as dienes in the Diels-Alder reaction" Tetrahedron Letters, 1993, 34, 4587-4590.
Chu, K.S.; Negrete, G.R.; Konopelski, J.P.; Lakner, F.J.; Woo, N.T.; Olmstead, M.M. "Enantiomerically pure dihydropyrimidinones as reagents and auxiliaries for asymmetric synthesis" Journal of the American Chemical Society, 1992, 114, 1800-1812.
Chu, K.S.; Negrete, G.R.; Konopelski, J.P. "Asymmetric total synthesis of (+)-jasplakinolide" Journal of Organic Chemistry, 1991, 56, 5196-5202.
Boehler, M.A.; Konopelski, J.P. "Enantiomerically pure vinylketene acetals in the Diels-Alder reaction - Catalysis and facial selectivity" Tetrahedron, 1991, 47, 4519-4538.
Smith, A.B.; Konopelski, J.P.; Wexler, B.A.; Sprengeler, P.A. "Quadrone structural and synthetic studies - Total synthesis of natural (-)-quadrone, the (+)-enantiomer, and the racemate - Conformational analysis, circular-dichroism, and determination of absolute stereochemistry" Journal of the American Chemical Society, 1991, 113, 3533-3542.
Negrete, G.R.; Konopelski, J.P. "Asymmetric alkylations of N-acyl dihydropyrimidinones" Tetrahedron Asymmetry, 1991, 2, 105-108.
Konopelski, J.P.; Chu, K.S.; Negrete, G.R. "Self-reproduction of chirality - Asymmetric synthesis of β-aryl-β-amino acids from enantiomerically pure dihydropyrimidinones" Journal of Organic Chemistry, 1991, 56, 1355-1357.
Eid, C.N.; Konopelski, J.P. "Acylketene acetals in organic synthesis" Tetrahedron, 1991, 47, 975-992.
Eid, C.N.; Konopelski, J.P. "Enantiomerically pure ketals in synthesis - Diastereoselective formation of β-keto and β-hydroxy ketals" Tetrahedron Letters, 1991, 32, 461-464.
Konopelski, J.P. "Conjugate addition reactions of enantiomerically pure acylketene acetals and ethyllithium. A pronounced salt effect" Tetrahedron Letters, 1991, 32, 465-466.
Fages, F.; Desvergne, J.P.; Bouas-Laurent, H.; Lehn, J.M.; Konopelski, J.P.; Marsau, P.; Barrans, Y. "Synthesis and fluorescence emission properties of a bis-anthracenyl macrotricyclic ditopic receptor. Crystal structure of its dinuclear rubidium cryptate" J. Chem. Soc., Chem. Commun., 1990, 655-658.
Eid, C.N.; Konopelski, J.P. "Conjugate hydroboration-reduction and organolithium additions to acylketene acetals. Synthesis of monoprotected beta-dicarbonyls" Tetrahedron letters, 1990, 31, 305-306.
1989 - 1980
Konopelski, J.P.; Boehler, M.A. "Enantiomerically pure vinyl ketene acetals as dienes in the Diels-Alder reaction" Journal of the American Chemical Society, 1989, 111, 4515-4517.
Konopelski, J.P.; Boehler, M.A.; Tarasow, T.M. "Preparation of (1R,2S)- and (11S,2R)- chloro-1,2-diphenylethanol and other β-halohydrins in enantiomerically pure form" Journal of Organic Chemistry, 1989, 54, 4966-4970.
Van Kuijk, F.J.; Thomas, D.W.; Konopelski, J.P.; Dratz, E.A. "Transesterification of phospholipids or triglycerides to fatty acid benzyl esters with simultaneous methylation of free fatty acids for gas-liquid chromatographic analysis" Journal of Lipid Research, 1986, 27, 452-456.
Guinand, G.; Marsau, P.; Lehn, J.M.; Kotzyba-Hibert, F.; Konopelski, J.P.; Desvergne, J.P.; Fages, F.; Castellan, A.; Bouas-Laurent, H. "Structures of two trichromophoric anthraceno cryptands" Acta Cryst., 1986, 715-719.
Konopelski, J.P.; Kotzyba-Hibert, F.; Lehn, J.M.; Desvergne, J.P.; Fages, F.; Castellan, A.; Bouas-Laurent, H. "Synthesis, cation binding, and photophysical properties of macrobicyclic anthraceno-cryptands" J. Chem. Soc., Chem. Commun., 1985, 433.
Smith, A.B.; Wexler, B.A.; Tu, C.Y.; Konopelski, J.P. "Stereoelectronic effects in the cationic rearrangements of [4.3.2]propellanes" Journal of the American Chemical Society, 1985, 107, 1308.
Smith, A.B.; Konopelski, J.P. "Total synthesis of (+)-quadrone: Assignment of absolute stereochemistry" Journal of Organic Chemistry, 1984, 49, 4094.
Konopelski, J.P.; Djerassi, C.; Raynaud, J.P. "Synthesis and biochemical screening of phenylselenium-substituted steroid hormones" Journal of Medicinal Chemistry, 1980, 23, 722.
Konopelski, J.P.; Djerassi, C. "Synthesis of chiral conformationally fixed cyclohexanones" Journal of Organic Chemistry, 1980, 45, 2297.
Konopelski, J.P.; Sundararaman, P.; Barth, G.; Djerassi, C. "Optical rotatory dispersion studies. 128. Octant contributions of methyl groups in 4-tert-butylcyclohexanones" Journal of the American Chemical Society, 1980, 102, 2737.
1979 - 1970
Konopelski, J.P.; Reimann, C.W.; Hubbard, C.R.; Mighell, A.D.; Santoro, A. "Hexakis(imidazole)nickel (II) chloride tetrahydrate" Acta Cryst., 1976, B32, 2911.
Hubbard, C.R.; Mighell, A.D.; Staffa, J.A.; Zervos, C.; Konopelski, J.P. "S-Carboxymethyl-l-cysteine sulfonate" Acta Cryst., 1976, B32, 2723.
Smith, D.H.; Konopelski, J.P.; Djerassi, C. "Applications of artificial intelligence for chemical interference. XIX - Computer generation of ion structures" Organic Mass Spectrometry, 1975, 11, 86.
