ΠΠ΅ΡΠ°Π»Π»ΠΎΠΊΠ°ΡΠ°Π»ΠΈΠ·ΠΈΡΡΠ΅ΠΌΡΠ΅ ΠΏΡΠ΅Π²ΡΠ°ΡΠ΅Π½ΠΈΡ Π°ΡΠ΅ΡΠΈΠ»Π΅Π½ΡΠΎΠ΄Π΅ΡΠΆΠ°ΡΠΈΡ ?-CF3-?-Π°ΠΌΠΈΠ½ΠΎΠΊΠΈΡΠ»ΠΎΡ, ΠΈΡ ΠΏΡΠΎΠΈΠ·Π²ΠΎΠ΄Π½ΡΡ ΠΈ ΡΠΎΡΡΠΎΡΠ½ΡΡ Π°Π½Π°Π»ΠΎΠ³ΠΎΠ²
Π‘ΠΈΡΡΠ΅ΠΌΠ°ΡΠΈΡΠ΅ΡΠΊΠΈ ΠΈΡΡΠ»Π΅Π΄ΠΎΠ²Π°Π½Π° ΡΠ΅Π°ΠΊΡΠΈΡ ΡΠ΅Π³ΠΈΠΎΡΠ΅Π»Π΅ΠΊΡΠΈΠ²Π½ΠΎΠΉ ΡΠΈΠΊΠ»ΠΎΡΡΠΈΠΌΠ΅ΡΠΈΠ·Π°ΡΠΈΠΈ ΠΏΠΎΠ»ΡΡΠ΅Π½Π½ΡΡ Π΄ΠΈΠΈΠ½ΠΎΠ² Ρ ΡΠ°Π·Π»ΠΈΡΠ½ΡΠΌΠΈ ΡΠ΅ΡΠΌΠΈΠ½Π°Π»ΡΠ½ΡΠΌΠΈ Π°Π»ΠΊΠΈΠ½Π°ΠΌΠΈ ΠΏΡΠΈ ΠΊΠ°ΡΠ°Π»ΠΈΠ·Π΅ ΠΊΠΎΠΌΠΏΠ»Π΅ΠΊΡΠ°ΠΌΠΈ ΡΡΡΠ΅Π½ΠΈΡ ΠΈ ΡΠΎΠ΄ΠΈΡ. ΠΡΠΈ ΡΡΠΎΠΌ Π½Π°ΠΉΠ΄Π΅Π½Ρ ΠΎΠΏΡΠΈΠΌΠ°Π»ΡΠ½ΡΠ΅ ΡΡΠ»ΠΎΠ²ΠΈΡ, Π½Π°ΠΈΠ±ΠΎΠ»Π΅Π΅ ΡΡΡΠ΅ΠΊΡΠΈΠ²Π½ΡΠ΅ ΠΊΠ°ΡΠ°Π»ΠΈΡΠΈΡΠ΅ΡΠΊΠΈΠ΅ ΡΠΈΡΡΠ΅ΠΌΡ, Π° ΡΠ°ΠΊΠΆΠ΅ ΠΏΡΠ΅Π΄Π»ΠΎΠΆΠ΅Π½ ΠΌΠ΅Ρ Π°Π½ΠΈΠ·ΠΌ ΡΠ΅Π°Π»ΠΈΠ·Π°ΡΠΈΠΈ Π΄Π°Π½Π½ΠΎΠ³ΠΎ ΠΏΡΠΎΡΠ΅ΡΡΠ° ΠΏΡΠΈ ΠΊΠ°ΡΠ°Π»ΠΈΠ·Π΅ ΡΡΡΠ΅Π½ΠΈΠ΅Π²ΡΠΌ ΠΊΠ°ΡΠ±Π΅Π½ΠΎΠ²ΡΠΌ ΠΊΠΎΠΌΠΏΠ»Π΅ΠΊΡΠΎΠΌ ΠΡΠ°Π±Π±ΡΠ° Π²ΡΠΎΡΠΎΠ³ΠΎ ΠΏΠΎΠΊΠΎΠ»Π΅Π½ΠΈΡ. Π ΡΠ΅Π·ΡΠ»ΡΡΠ°ΡΠ΅… Π§ΠΈΡΠ°ΡΡ Π΅ΡΡ >
Π‘ΠΏΠΈΡΠΎΠΊ Π»ΠΈΡΠ΅ΡΠ°ΡΡΡΡ
- F. J. Sardina, Π. Rapoport, Enantiospecific synthesis of heterocycles from a-amino acids // Chem. Rev. 1996. — Vol. 96. — p. 1825−1872.
- S. Hanessian, G. McNaughton-Smith, H. G. Lombart, W. D. Lubell, Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics // Tetrahedron. 1997. — Vol. 53. — p. 12 789−12 854.
- G. M. Coppola, H. F. Schuster, Asymmetric synthesis: construction of chiral molecules using amino acids, Wiley, New York, 1987.
- Comprehensive Asymmetric Catalysis, eds. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, 2000.
- R. M. Williams, D. J. Aldous, S. C. Aldous, Synthesis of ethynylglycine // J. Chem. Soc. Perkin Trans. 1. 1990. — p. 171−172.
- R. M. Williams, D. J. Aldous, S. C. Aldous, General synthesis of p, y-alkynylglycine derivatives II J. Org. Chem. 1990. — Vol. 55. — p. 4657−4663.
- P. J. Casara, B. W. Metcalf, Trimethylsilylacetylene-N-carboethoxy glycinate dianion a general synthon for a-acetylenic a-amino acids // Tetrahedron Lett. — 1978. — Vol. 18. — p. 15 811 584.
- J.-X. Ji, T. T.-L. Au-Yeung, J. Wu, C. W. Yip, A. S. C. Chan, Efficient synthesis of alkynyl a-amino acid derivatives by Ag (I)-catalyzed alkynylation of a-imino esters // Adv. Synth. Catal. 2004. — Vol. 346 — p. 42−44.
- Z. Shao, A. S. C. Chan, Copper (I)-catalyzed three-component coupling leading to an efficient synthesis of P, y-alkynyl a-amino acid derivatives // Synthesis 2008. — p. 2868−2870.
- P. Meffre, L. Gauzy, E. Branquet, P. Durand, F. L. Goffic, Synthesis of Optically Active P, y-Alkynylglycine Derivatives // Tetrahedron 1996. — Vol. 52. — p. 11 215−11 238.
- M. Rueping, A. P. Antonchick, C. Brinkmann, Dual xatalysis: a combined enantioselective Bronsted acid and metal-catalyzed reaction—metal catalysis with chiral counterions // Angew. Chem. Int. Ed. 2007. — Vol. 46. — p. 6903 -6906.
- H. Kagoshima, T. Uzawa, T. Akiyama, Catalytic, enantioselective propargyl- and allenylation reactions of a-imino ester // Chemistry Letters. 2002. — p. 298−299.
- H. Itoh, S. Matsuoka, M. Kreir, M. Inoue, Design, synthesis and functional analysis of dansylated polytheonamide mimic: an artificial peptide ion channel // J. Am. Chem. Soc. 2012. -Vol. 134.-p. 14 011−14 018.
- H. Gershon, J. Shapira, J. S. Meek, K. Dittmer, The syntheses and microbiological properties of acetylenic amino acids. Propargylglycine and 2-amino-3-methyl-4-pentynoic acid // J. Am. Chem. Soc. 1954. — Vol. 76. — p. 3484.
- B. Kubel, P. Gruber, R. Hurnuus, W. Steglich, a-Substituierte a-aminosauren durch alkylierung von oxazolin-5-onen // Chem. Ber. 1979. — Vol. 112. — p. 128−137.
- M. J. Sofia, P. K. Chakravarty, J. A. Katzenellenbogen, Synthesis of five-membered halo enol lactone analogues of a-amino acids: potential protease suicide substrates // J. Org. Chem. -1983. Vol. 48. — p. 3318−3325.
- S. Kotha, N. Sreenivasachary, A new synthetic approach to 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives via enyne metathesis and the Diels-Alder reaction // Chem. Commun. 2000. — p. 503−504.
- S. Kotha, S. Haider, E. Brahmachary, Synthesis of highly functionalized phenylalanine derivatives via cross-enyne metathesis reactions // Tetrahedron. 2002. — Vol. 58. — p. 92 039 208.
- R. J. Brea, M. P. Lopez-Deber, L. Castedo, J. R. Granja, Synthesis of co-(hetero)arylalkynylated a-amino acid by Sonogashira-type reactions in aqueous media // J. Org. Chem. 2006. — Vol. 71. — p. 7870−7873.
- R. Chinchilla, C. Najera, The Sonogashira reaction: a booming methodology in synthetic organic chemistry // Chem. Rev. 2007. — Vol. 107. — p. 874−922.
- R. Chinchilla, C. Najera, Recent advances in Sonogashira reactions // Chem. Soc. Rev. — 2011. Vol. 40. — p. 5084−5121.
- B. C. J. van Esseveldt, F. L. van Delft, J. M. M. Smits, R. de Gelder, F. P. J. T. Rutjes, Pd-catalysed synthesis of 5-substituted proline derivatives from acetylene-containing amino acids // Synlett. 2003. — p. 2354−2358.
- D. W. Knight, A. L. Redfern, J. Gilmore, An approach to 2,3-dihydropyrroles and f3-iodopyrroles based on 5-endo-dig cyclisations // J. Chem. Soc., Perkin Trans. 1. 2002. — p. 622−628.
- G. T. Crisp, Y.-L. Jiang, Intramolecular hydrogen bonding studies for a series of dipurinyl-2,6-pyridinedicarboxamides // Tetrahedron. 1999. — Vol. 55. — p. 549.
- G. Lassalle, J. M. Altenburger, SSR182289A, a selective and potent orally active thrombin inhibitor // Bioorg. Med. Chem. 2004. — Vol. 12. — p. 1713.
- R. J. Brea, M. P. Lopez-Deber, L. Castedo, J. R. Granja, Synthesis of o-(Hetero)arylalkynylated a-amino acid by Sonogashira-type reactions in aqueous media // J. Org. Chem. 2006. — Vol. 71. — p. 7870.
- Y. Du, C. J. Creighton, Z. Yan, D. A. Gauthier, J. P. Dahl, B. Zhao, S. M. Belkowski, A. B. Reitz, The synthesis and evaluation of 10- and 12-membered ring benzofused enediyne amino acids // Bioorg. Med. Chem. 2005. — Vol. 13 — p. 5936.
- H. Villar, M. Fringsa, C. Bolm. Ring closing enyne metathesis: A powerful tool for the synthesis of heterocycles // Chem. Soc. Rev. 2007. — Vol. 36. — p. 55.
- S. T. Diver, A. J. Giessert, Enyne metathesis (enyne bond reorganization) // Chem. Rev. -2004.-Vol. 104.-p. 1317−1382.
- M. Mori, Synthesis of natural products and related compounds using enyne metathesis // Adv. Synth. Catal. 2007. — Vol. 349. — p. 121 — 135.
- M. Mori, Recent progress on enyne metathesis: its application to syntheses of natural products and related compounds // Materials. 2010. — Vol. 3. — p. 2087−2140.
- M. Mori, N. Sakakibara, A. Kinoshita, Remarkable effect of ethylene gas in the intramolecular enyne metathesis of terminal alkynes. J. Org. Chem. 1998. — Vol. 63. — p. 6082.
- N. Chatani, H. Inoue, T. Kotsuma, S. Murai, Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl3 // J. Am. Chem. Soc. 2002. — Vol. 124. — p. 10 294.
- T. Kitamura, Y. Satom, M. Mori, Synthetic study of (C)-anthramycin using ring-closing enyne metathesis and cross-metathesis // Tetrahedron. 2004. — Vol. 60. — p. 9649.
- H. Fukumoto, K. Takahashi, J. Ishihara, S. Hatakeyama, Total synthesis of (+)-b-erythroidine // Angew. Chem. Int. Ed. 2006. — Vol. 45. — p. 2731.
- G. B. Hoven, J. Efskind, C. Romming, K. Undheim, Ru (II)-catalyzed cascade reactions in stereocontrolled construction of rigid as-indacene-bridged bis (a-amino acid) derivatives // J. Org. Chem. 2002. — Vol. 67. — p. 2459.
- M. D. Middleton, B. P. Peppers, S. T. Diver, Studies directed toward the synthesis of the scabrosins: validation of a tandem enyne metathesis approach // Tetrahedron. 2006. — Vol. 62 -p. 10 528−10 540.
- A. A. Kulkarni, S. T. Diver, Ring synthesis by stereoselective, methylene-free enyne cross metathesis // J. Am. Chem. Soc. 2004. — Vol. 126. — p. 8110−8111.
- S. Kotha, M. Meshram, A. Tiwari, Advanced approach to polycyclics by a synergistic combination of enyne metathesis and Diels-Alder reaction // Chem. Soc. Rev. 2009. — Vol. 38. — p. 2065−2092.
- S. Kotha, N. Sreenivasachary, A new synthetic approach to 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives via enyne metathesis and the Diels-Alder reaction // Chem. Commun. 2000. — p. 503−504.
- S. Kotha, P. Khedkar, Synthesis of a conformationally constrained phenylalanine derivative by a strategic combination of ring-closing enyne metathesis and Diels-Alder reaction // Synthesis. 2008. — p. 2925−2928.
- S. Kotha, N. Sreenivasachary, E. Brahmachary, Constrained phenylalanine derivatives by enyne metathesis and Diels-Alder reaction // Eur. J. Org. Chem. 2001. — p. 787.
- S. Kotha, K. Mandal, S. Banerjee, S. M. Mobin, Synthesis of novel quinone-amino acid hybrids via cross-enyne metathesis and Diels-Alder reaction as key steps // Eur. J. Org. Chem. — 2007.-p. 1244−1255.
- J. Efskind, C. Romming, K. Undheim, Stereocontrolled construction of rigid tricyclic bis (a-amino acid) derivatives by Ru (II)-catalyzed cascade and Diels-Alder reactions // J. Chem. Soc., Perkin Trans. 1. 2001. — p. 2697−2703.
- D. Semeril, J. Le Notre, C. Bruneau, P. H. Dixneuf, A. F. Kolomiets, S. N. Osipov,
- Fluorine-containing a-alkynyl amino esters and access to a new family of 3,4-dehydroprolineanalogues // New J. Chem. 2001. — Vol. 25. -p. 16−18.114
- O.Geis, H. G., Schmalz, New developments in the Pauson-Khand reaction // Angew. Chem., Int. Ed. 1998. — Vol. 37. — p. 911.
- Chung, Y. K., Transition metal alkyne complexes: the Pauson-Khand reaction // Coord. Chem. Rev. 1999. — Vol. 188. — p. 297.
- K. M. Brummond, J. L. Kent, Recent advances in the Pauson-Khand reaction and related 2+2+1. cycloadditions // Tetrahedron 2000. — Vol. 56. — p. 3263.
- H.-W. Lee, F.-Y. Kwong, A decade of advancements in Pauson-Khand-type reactions // Eur. J. Org. Chem. -2010. p. 789.
- L. Perez-Serrano, L. Casarrubios, G. Dominguez, J. Perez-Castells, Pauson-Khand reaction induced by molecular sieves // Org. Lett. 1999. — Vol. 1. — p. 1187.
- J. Blanco-Urgoiti, L. Casarrubios, G. Dominguez, J. Perez-Castells, New protocol for the catalytic Pauson-Khand reaction induced by molecular sieves // Tetrahedron Lett. 2002. — Vol. 43.-p. 5763.
- M. E. Krafft, L. V. R. Bosaga, C. Hirosawa, Cobalt carbonyl-mediated carbocyclizations of enynes: generation of bicyclooctanones or monocyclic alkenes // J. Org. Chem. 2002. — Vol. 67.-p. 1233.
- M. K. Pallerla, J. M. Fox, Enantioselective synthesis of (-)-pentalenene // Org. Lett. -2007. Vol. 26. — p. 5625.
- T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, Tandem use of cobalt-mediated reactions to synthesize (+)-Epoxydictymene, a Diterpene Containing a Trans-Fused 5−5 Ring System II J. Am. Chem. Soc. 1997. — Vol. 119. — p. 4353.
- T. Honda, K. Kaneda, Diastereoselective Formal synthesis of a monoterpene alkaloid, (-)-incarvilline // J. Org. Chem. 2007. — Vol. 72. — p. 6541.
- G. Magueur, J. Legros, F. Meyer, M. Ourevitch, B. Crousse, D. Bonnet-Delpon, A one-pot synthesis of doubly unsaturated trifluoromethyl amines: easy access to CF3-substituted piperidines // Eur. J. Org.Chem. 2005. — p. 1258.
- B. Jiang, M. Xu, Catalytic diastereoselective Pauson-Khand reaction: an efficient route to enantiopure cyclopentac. proline derivatives // Org. Lett. 2002. — Vol. 4. — p. 4077−4080.
- B. Witulski, M. GoBmann, Stereospecific synthesis of chiral N-(ethynyl)allylglycines and their use in highly stereoselective intramolecular Pauson-Khand reactions // Chem. Commun. -1999.-p. 1879−1880.
- Y. Li, M.-H. Xu, Lewis acid promoted highly diastereoselective petasis borono-mannich reaction: efficient synthesis of optically active j3, y-unsaturated a-amino acids // Org. Lett. -2012. Vol. 14. — p. 2062−2065.
- B. Jiang, M. Xu, Highly enantioselective construction of fused pyrrolidine systems that contain a quaternary stereocenter: concise formal synthesis of (+)-conessine // Angew. Chem. Int. Ed. 2004. — Vol. 43. — p. 2543−2546.
- S. Saito, Y. Yamamoto, Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives // Chem. Rev. 2000. — Vol. 100. — p. 29 012 916.
- J.A. Varela, C. Sara, Construction of pyridine rings by metal-mediated 2+2+2. cycloaddition II Chem. Rev. 2003. — Vol. 103. — p. 3787−3802-
- Y. Yamamoto, Recent advances in intramolecular alkyne cyclotrimerization and its applications // Curr. Org. Chem. 2005. — Vol. 9. — p. 503−519-
- B. Heller, M. Hapke, The fascinating construction of pyridine ring systems by transition metal-catalysed 2+2+2. cycloaddition reactions // Chem. Soc. Rev. 2007. — Vol. 36. — p. 10 851 094-
- N. Agenet, O. Buisine, F. Slowinski, V. Gandon, C. Aubert, M. Malacria, Cotrimerizations of acetylenic compounds // Org. React. 2007. — Vol. 68. — p. 1-
- J.A. Varela, C. Sara, Recent advances in the synthesis of pyridines by transition metal-catalyzed 2+2+2. cycloaddition // Synlett. 2008. — p. 2571−2578-
- T. Shibata, K. Tsuchikama, Recent advances in enantioselective 2+2+2. cycloaddition // Org. Biomol. Chem. -2008. Vol. 6. — p. 1317−1323-
- B.R. Galan, T. Rovis, Beyond Reppe: building substituted arenes by 2+2+2.cycloadditions of alkynes II Angew. Chem. Int. Ed. 2009. — Vol. 48. — p. 2830−2834−116
- G. Dominguez, J. Perez-Castells, Recent advances in 2+2+2. cycloaddition reactions // Chem. Soc. Rev. 2011. — Vol. 40. — p. 3430−3444-
- P.R. Chopade, J. Louie, 2+2+2. Cycloaddition reactions catalyzed by transition metal complexes II Adv. Synth. Catal. 2006. — Vol. 348, p. 2307−2327-
- S. Kotha, E. Brahmachary, K. Lahiri, Transition metal catalyzed 2+2+2. cycloaddition and application in organic synthesis // Eur. J. Org. Chem. 2005. — p. 4741−4767.
- W. Whaley, T. R. Govindachari, The Pictet-Spengler synthesis oftetrahydroisoquinolines and related compounds // Org. React. 1951. — Vol. 6. — p. 152−187.
- W. Whaley, T. R. Govindachari, The preparation of 3,4-dihydroisoquinolines and related compounds by the Bischler-Napieralski reaction // Org. React. 1951. — Vol. 6. — p. 74−150.
- W. J. Gensler, The synthesis of isoquinolines by the Pomeranz-Fritsch reaction // Org. React. 1951. — Vol. 6. — p. 151−206.
- S. Kotha, K. Mohanraja, S. Durani, Constrained phenylalanyl peptides via a 2+2+2.-cycloaddition strategy // Chem. Commun. 2000. — p. 1909−1910-
- S. Kotha, E. Brahmachary, Synthesis of constrained phenylalanine derivatives via a 2+2+2. cycloaddition strategy // Bioorg. Med. Chem. 2002. — Vol. 10. — p. 2291−2295-
- S. Kotha, E. Brahmachary, Synthesis and reactions of silicon containing cyclic a-amino acid derivatives // Journal of Organomet. Chem. 2004. — Vol. 689. — p. 158−163-
- S. Kotha, N. Sreenivasachary, Synthesis of l, 2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives by cycloaddition approaches // Eur. J. Org. Chem. 2001. — p. 3375−3383-
- L. Garcia, A. Pla-Quintana, A. Roglans, Synthesis of non-proteinogenic phenylalanine derivatives by rhodium-catalyzed 2+2+2. cycloaddition reactions // Org. Biomol. Chem. 2009. -Vol. 7.-p. 5020−5027.
- N. T. Patil, Y. Yamamoto, Coinage metal-assisted synthesis of heterocycles // Chem. Rev. 2008. — Vol. 108. — p. 3395−3442-
- I. Nakamura, Y. Yamamoto, Transition-metal-catalyzed reactions in heterocyclic synthesis // Chem. Rev. 2004. — Vol. 104. — p. 2127−2198-
- L. B. Wolf, K. C. M. F. Tjen, H. T. ten Brink, R. H. Blaauw, H. Hiemstra, H. E. Schoemaker, F. P. J. T. Rutjes, Palladium-catalyzed cyclization reactions of acetylene-containing amino acids II Adv. Synth. Catal. 2002. Vol. 344. — p. 70−83.
- B. C. J. van Esseveldt, F. L. van Delft, R. de Gelder, F. P. J. T. Rutjes, Palladium-catalyzed synthesis of novel optically active tryptophan analogues // Org. Lett. 2003. — Vol. 5. -p. 1717−1720.
- H. Wu, Y. He, L. Gong, The combination of relay and cooperative catalysis with a gold/pa 1 ladium/Bransted acid ternary system for the cascade hydroamination/allylic alkylation reaction II Adv. Synth. Catal. -2012. Vol. 354. — p. 975 — 980.
- H. C. Kolb, M. G. Finn, K. B. Sharpless, Click chemistry: diverse chemical function from a few good reactions // Angew. Chem. Int. Ed. — 2001. Vol. 40. — p. 2004.
- C. W. Tornoe, C. Christensen, M. Meldal, Peptidotriazoles on solid phase: 1,2,3.-triazoles by regiospecific copper (I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides // J. Org. Chem. 2002. — Vol. 67. — p. 3057.
- N. G. Angelo, Paramjit S. Arora, Nonpeptidic foldamers from amino acids: synthesis and characterization of 1,3-substituted triazole oligomers // J. Am. Chem. Soc. 2005. — Vol. 127. -p.17 134−17 135.
- N.J. Stanley, D. S. Pedersen, B. Nielsen, T. Kvist, J.M. Mathiesen, H. Brauner-Osborne, D.K. Taylor, A.D. Abell, 1,2,3-Triazolyl amino acids as AMPA receptor ligands // Bioorg. Med. Chem. Lett. 2010. — Vol. 20. — p. 7512−7515.
- G.T. Shchetnikov, A.S. Peregudov, S.N. Osipov, Effective pathway to the a-CF3-substituted azahistidine analogues // Synlett. 2007. — p. 136.
- A. Alix, S. Chassaing, P. Pale, J. Sommer, 'Click chemistry' in Cul-zeolites: a convenient access to glycoconjugates // Tetrahedron. 2008. — Vol. 64. — p. 8922−8929.
- C. Proulx, W. D. Lubell, Aza-l, 2,3-triazole-3-alanine synthesis via copper-catalyzed 1,3-dipolar cycloaddition on aza-progargylglycine // J. Org. Chem. 2010. — Vol. 75. — p. 53 855 387.
- J.P. Genet, J. Uziel, M. Port, A.M. Touzin, S. Roland, S. Thorimbert, S. Tanier, A practical synthesis of a-aminophosphonic acids // Tetrahedron Letters — 1992. Vol. 33. — p. 77−80.
- R. Dodda, C.-G. Zhao, Silver (I) triflate-catalyzed direct synthesis of N-PMP protected a-aminopropargylphosphonates from terminal alkynes // Org. Lett. — 2007. Vol. 9. — p. 165−167.
- R. Dodda, C.-G. Zhao, Enantioselective synthesis of a-aminopropargylphosphonates 11 Tetrahedron Letters. 2007. — Vol. 48. — p. 4339−4342.
- Π’. K. Sawyer in Structure-Based Drug Design: Disease, Targets, Techniques and Development (Ed.: P. Veerapandian), Marcel Dekker, New York, 1997, p. 559−634-
- J. A. Patch, K. Kirshenbaum, S. L. Seurynck, R. N. Zuckermann, A. E. Barron in Pseudopeptides in Drug Development (Ed.: P. E. Nielsen), Wiley-VCH, Weinheim, 2004.
- V. J. Hruby, G. Li, C. Haskell-Luevano, M. D. Shenderovich, Design of peptides, proteins, and peptidomimetics in chi space II Biopolymers. 1997. — Vol. 43. — p. 219−266.
- H. Vogt, S. Brase, Recent approaches towards the asymmetric synthesis of a, a-disubstituted a-amino acids // Org. Biomol. Chem. 2007. — Vol. 5. — p. 406−430.
- B. Koksch, N. Sewald, H.-D. Jakubke, K. Burger in Biochemical Frontiers of Fluorine Chemistry (Eds.: I. Ojima, J. R. McCarthy, J. T. Welch), ACS Symposium Series No. 639, ACS, Washington DC, 1996, p. 42.
- K. Uneyama, Organofluorine Chemistry, Blackwell Publishing Ltd., 2006.
- N. Sewald, K. Burger in Synthesis of ?-Fluoro-Containing Amino Acids (Eds.: V. P Kukhar, V. A. Soloshonok), John Wiley & Sons Ltd., 1995, p. 139−220.
- N. C. Yoder, K. Kumar, Fluorinated amino acids in protein design and engineering // Chem. Soc. Rev. 2002. — Vol. 31. — p. 335−341.
- C. Jaeckel, M. Salwiczek, B. Koksch, Fluorine in a native protein environment—how the spatial demand and polarity of fluoroalkyl groups affect protein folding // Angew. Chem. Int. Ed. 2006. — Vol. 45. — p. 4198^1203.
- Π‘. Π. ΠΠ±Π΄ΡΠ»Π³Π°Π½Π΅Π΅Π²Π°, Π. Π. ΠΡΠΆΠ°Π½ΠΎΠ², ΠΡΠ΅ΡΠΈΠ»Π΅Π½ΠΎΠ²ΡΠ΅ Π°ΠΌΠΈΠ½ΠΎΠΊΠΈΡΠ»ΠΎΡΡ // Π£ΡΠΏΠ΅Ρ ΠΈ Ρ ΠΈΠΌΠΈΠΈ. — 1991.-Vol. 60.-Ρ. 1318−1342.
- S. N. Osipov, A. S. Golubev, N. Sewald, Π’. Michel, Π. F. Kolomiets, Π. V. Fokin, Π. Burger, A new strategy for the synthesis of a-difluoromethyl-substituted a-hydroxy and a-amino acids II J. Org. Chem. 1996. — Vol. 61. — p. 7521−7528.
- C. Glaser, Beitrage zur Kenntniss des Acetenylbenzols II Ber. Dtsch. Chem. Ges. — 1869. -Vol. 2.-p. 422−424.
- J. Li, Y. Liang, Y. Xie, Efficient palladium-catalyzed homocoupling reaction and Sonogashira cross-coupling reaction of terminal alkynes under aerobic conditions // J. Org. Chem. 2005. — Vol. 70. — p. 4393−4396.
- G. T. Shchetnikov, M. A. Zotova, C. Bruneau, P. H. Dixneuf, S. N. Osipov, Synthesis of a-alkynyl-?,?,?-trifluoroalamne derivatives by Sonogashira cross-coupling reaction // Eur. J. Org. Chem. 2010. — p. 1587−1592.
- F.R. Atherton, C.H. Hassall, R. W. Lambert, Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (l-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid // J. Med. Chem. 1986. — Vol. 29. — p. 29−40.
- J. G. Allen, F. R. Atherton, M. J. Hall, C. H. Hassal, S. W. Homes, R. W. Lambert, L. J. Nisbet, P. S. Ringrose, Phosphonopeptides, a new class of synthetic antibacterial agents // Nature 1978.-Vol. 272.-p. 56−58.
- P. P. Ginnousis, P. A. Bartlett, Phosphorus amino acid analogs as inhibitors of leucine aminopeptidase II J. Med. Chem. 1987. — Vol. 30. — p. 1603−1609.
- M. C. Allen, W. Fuhrer, B. Tuck, R. Wade, J. M. Wood, Renin inhibitors. Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond // J. Med. Chem. 1989. — Vol. 32. — p. 1652−1661.
- A. Peyman, K.-H. Budt, J. Spanig, B. Stowasser, D. Ruppert, C2-symmetric phosphinic acid inhibitors of HIV protease // Tetrahedron Lett. 1992. — Vol. 33. — p. 4549−4552.
- A. Peyman, W. Stahl, K. Wagner, D. Ruppert, K.-H. Budt, Non-peptide-based inhibitors of human immunodeficiency virus-1 protease // Bioorg. Med. Chem. Lett. 1994. — Vol. 4. — p. 2601−2604.
- M. A. Zotova, T. P. Vasilyeva, A. S. Peregudov, S. N. Osipov, Synthesis of CF3-containing a-alkynyl-a-aminophosphonates by Sonogashira cross-coupling reaction // J. Fluorine Chem. 2012. — p. 33−37.
- J. R. Del Valle, M. Goodman, Asymmetric hydrogenations for the synthesis of Boc-protected 4-alkylprolinols and prolines // J. Org. Chem. 2003. — Vol. 68. — p. 3923−3931.
- N. Pellegrini, M. Schmitt, J.-J. Bourguignon, Rapid access to cis 3-substituted prolines // Tetrahedron Lett. 2003. — Vol. 44. — p. 6779 — 6780.
- J. Zhang, W. Wang, C. Xiong, V. J. Hruby, Efficient and stereoselective synthesis of novel cw^-substituted proline analogues // Tetrahedron Lett. 2003. — Vol. 44. — p. 1413 -1415.
- J. R. Del Valle, M. Goodman, Stereoselective synthesis of Boc-protected cis and trans-4-trifluoromethylprolines by asymmetric hydrogenation reactions // Angew. Chem., Int. Ed. 2002. -Vol. 41.-p. 1600- 1602.
- Q. Xia, B. Ganem, An efficient synthesis of substituted prolines by the selective reduction and reductive cyanation of 2-pyrrolidones // Tetrahedron Lett. 2002. — Vol. 43. — p. 1597- 1598.
- C. Flamant-Robin, Q. Wian, A. Chiaroni, N. A. Sasaki, An efficient method for the stereoselective synthesis of cis-3-substituted prolines: conformationally constrained a-amino acids // Tetrahedron. 2002. — Vol. 45. — p. 10 475 — 10 484.
- M. Nevalainen, P. M. Kauppinen, A. M. P. Koskinen, Synthesis of Fmoc-protected trans-4-methylproline // J. Org. Chem. 2001. — Vol. 66. — p. 2061 — 2066.
- T. M. Kamenecka, Y.-J. Park, L. S. Lin, T. Jr. Lanza, W. K. Hagmann, Enantioselective approach to 3-substituted prolines // Tetrahedron Lett. 2001. — Vol. 42. — p. 8571 — 8573.
- D. Damour, F. Herman, R. Labaudinie’re, G. Pantel, M. Vuilhorgne, S. Mignani, Synthesis of novel proline and |/-lactam derivatives as non-peptide mimics of Somatostatin/Sandostatin® // Tetrahedron. 1999. — Vol. 55. — p. 10 135−10 154.
- K. K. Schumacher, J. Jiang, M. M. Joullie, Synthetic studies toward astins A, B and C. Efficient syntheses of cis-3,4-dihydroxyprolines and (-)-(3S, 4R)-dichloroproline esters // Tetrahedron: Asymmetry 1998. — Vol. 9. — p. 47−53.
- Y. Xu, J. Choi, M. I. Calaza, S. Turner, H. Rapoport, Conformationally constrained nicotines. l-Pyridinyl-7-azabicyclo2.2.1.heptane and l-pyridinyl-8-azabicyclo[3.2.1]octane analogues // J. Org. Chem. 1999. — Vol. 64. — p. 4069−4078.
- E. Kato, K. Yamamoto, Y. Kawashima, T. Watanabe, M. Oya, T. Iso, J. Iwao, Synthesis and antihypertensive activity of 5-(2-hydroxyphenyl)-l-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acids // Chem. Pharm. Bull. 1985. — Vol. 33. — p. 4836−4846.
- F. Manfre, J. P. Pulicani, Enantiospecific synthesis and absolute configuration of (+)-RP 66 803 a new non-peptide CCK antagonist // Tetrahedron: Asymmetry 1994. — Vol. 5. — p. 235 238.
- B. C. J. van Esseveldt, P. W. H. Vervoort, F. L. van Delft, F. P. J. T. Rutjes, Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key step II J. Org. Chem. -2005.-Vol. 70.-p. 1791−1795.
- P. Kafarski, B. Lejczak, Aminophosphonic acids of potential medical importance // Curr. Med. Chem. Anticancer Agents 2001. — Vol. 1. — p. 301 -312.
- J. Grembecka, P. Kafarski, Leucine aminopeptidase as a target for inhibitor design // Mini Rev. Med. Chem. -2001. -Vol. l.-p. 133−144.
- D. L. Mohler, G. Shen, The synthesis of tethered ligand dimers for PPARy-RXR protein heterodimers // Org. Biomol. Chem. 2006. — Vol. 4. — p. 2082−2087.
- F. Nissen, H. Detert, Total synthesis of Lavendamycin by a 2+2+2. cycloaddition // Eur. J. Org. Chem. 2011. — p. 2845−2853.
- T. Welsch, H.-A. Tran, B. Witulski, Total Syntheses of the Marine Illudalanes Alcyopterosin I, L, M, N, and C // Org. Lett. 2010. — Vol. 12. — p. 5644−5647.
- I. Gavras, D. Vlahakos, J. C. Melby, H. Gavras, Pilot study of the effects of the angiotensin-converting enzyme inhibitor CI-906 on patients with essential hypertension // J. Clin. Pharm. 1984. — Vol. 24. — p. 343−350.
- G. Francois, G. Bringmann, J. D. Phillipson, M. R. Boyd, L. A. Assi, C. Schneider, G. Timperman, U.S. Patent β. 5, 639, 761, 1994.
- T. Asaoka, K. Yazawa, Y. Mikami, T. Arai, K. Takahashi, A new saframycin, saframycin R. // J. Antibiot. 1982. — Vol. 35. — p. 1708−1710.
- S. Vendeville, F. Goossens, M. A. Debreu-Fontaine, V. Landry, E. Davioud-Charvet, P.
- Grellier, S. Scharpe, G. Sergheraert, Comparison of the inhibition of human and trypanosomacruzi prolyl endopeptidases // Bioorg. Med. Chem. 2002. — Vol. 10. — p. 1719−1729.122
- A. Wang, D. C. U’Prichard, V. J. Marder, US Patent β. 61 885 Al, 2002.
- G. Balboni, S. Fiorini, A. Baldisserotto, C. Trapella, Y. Sasaki, A. Ambo, E. D. Marczak, L. H. Lazarus, S. Salvadori, Further studies on lead compounds containing the opioid pharmacophore Dmt-Tic // J. Med. Chem. 2008. — Vol. 51. — p. 5109−5117.
- N. A. Markina, R. Mancuso, B. Neuenswander, G. H. Lushington, R.C. Larock, Solution-phase parallel synthesis of a diverse library of 1,2-dihydroisoquinolines // ACS Comb. Sci. -2011.-Vol. 13.-p. 265−271.
- G. T. Shchetnikov, S. N. Osipov, C. Bruneau, P. H. Dixneuf, Ruthenium-catalyzed cyclotrimerization of 1,6- and 1,7-azadiynes: new access to fluorinated bicyclic amino acids // Synlett. 2008. — Vol. 4. — p. 578−582.
- K. Kirchner, M. J. Calhorda, R. Schmid, L. F. Veiros, Mechanism for the cyclotrimerization of alkynes and related reactions catalyzed by CpRuCl // J. Am. Chem. Soc. -2003. Vol. 125. — p. 11 721−11 729.
- J.-U. Peters, Ruthenium-catalyzed conversion of triynes to benzene derivatives — a novel metathesis cascade// Chem. Commun. 1997. — p. 1983−1984.
- B. Witulski, T. Stengel, J. M. Fernandez-Hernandez, Chemo- and regioselective crossedalkyne cyclotrimerisation of 1,6-diynes with terminal monoalkynes mediated by Grubbs' catalystor Wilkinson’s catalyst // Chem. Commun. 2000. — p. 1965−1966.123
- S. Greau, B. Radetich, T. V. RajanBabu, First demonstration of helical chirality in 1,4-disubstituted (Z, Z)-l, 3-dienes: R3Si-SnR'3-mediated cyclization of 1,6-diynes // J. Am. Chem. Soc. 2000. — Vol. 122. — p. 8579−8580.
- C. Czekelius, J. Hafer, Z. J. Tonzetich, R. R. Schrock, R. L. Christensen, P. Muller, Synthesis of oligoenes that contain up to 15 double bonds from 1,6-heptadiynes // J. Am. Chem. Soc. 2006. — Vol. 128. — p. 16 664−16 675.
- Christian Bruneau, Pierre H. Dixneuf (Universite de Rennes)-ΠΌΠΎΠ΅ΠΌΡ Π±ΠΎΠ΅Π²ΠΎΠΌΡ ΡΠΎΠ²Π°ΡΠΈΡΡ ΠΡΡΡΡΡ ΠΠ°ΠΈΠ»ΡΠ½Ρ Π·Π° ΡΠΎ, ΡΡΠΎ Π²ΡΠ΅Π³Π΄Π° ΠΏΠΎΠΌΠΎΠ³Π°Π» ΠΌΠ½Π΅ ΠΈ Π½Π΅ Π΄Π°Π²Π°Π» ΡΠΏΠ°ΡΡΡ Π΄ΡΡ ΠΎΠΌ-
- Π ΠΎΠΌΠ°Π½Ρ ΠΠΎΠ²ΠΈΠΊΠΎΠ²Ρ Π·Π° ΡΡΠ΄Π΅ΡΠ½ΡΠ΅ Π―ΠΠ -ΡΠΏΠ΅ΠΊΡΡΡ- ΠΠ½ΡΠΎΠ½Ρ ΠΠΈΠΆΠΈΠ½Ρ Π·Π° Π΄ΡΡΠΆΠ΅ΡΠΊΠΎΠ΅ ΡΡΠ°ΡΡΠΈΠ΅-
- ΠΠ»Π°Π΄ΠΈΠΌΠΈΡΡ ΠΠ΅Π²ΠΎΡΠ³ΡΠ½Ρ Π·Π° ΠΈΠ½ΡΠ΅ΡΠ΅ΡΠ½ΡΠ΅ Π΄ΠΎΠΊΠ»Π°Π΄Ρ ΠΈ Π±Π΅ΡΠ΅Π΄Ρ Π½Π° ΠΊΠΎΠ½ΡΠ΅ΡΠ΅Π½ΡΠΈΡΡ ΠΈ Π·Π° Π²Π½ΠΈΠΌΠ°Π½ΠΈΠ΅ ΠΊ ΠΌΠΎΠ΅ΠΉ ΡΠ°Π±ΠΎΡΠ΅-Π° ΡΠ°ΠΊΠΆΠ΅:
- Π. Π. ΠΠ΅ΠΌΠ΅Π½ΠΎΠ²ΡΠΊΠΎΠΌΡ, Π. Π. Π§Π΅ΠΏΡΠ°ΠΊΠΎΠ²Ρ, Π. Π. Π’ΡΠΎΡΠΈΠΌΠΎΠ²ΠΎΠΉ, Π. Π. Π€Π΅Π΄ΠΎΡΠΎΠ²Ρ, Π. Π. ΠΡΠΊΡ, J1. Π. ΠΠΈΠ²Π°Π½ΡΠΎΠ²ΠΎΠΉ- Π‘. Π. ΠΠ΅ΡΡΠ΄ΠΎΠ²Ρ-