Facile preparation of the tosylhydrazone derivatives of a series of racemic trans-3,4-substituted cyclopentanones

Molecules

Volumn 17, Issue 1, 2012, Pages 1-14

  Bouhadir, Kamal H ^a   Aleiwe, Bilal Abou ^a   Fares, Fares A ^a,b  

^a AMERICAN UNIVERSITY OF BEIRUT   (Lebanon)

^b LEBANESE UNIVERSITY   (Lebanon)

Author keywords

Cyclopentanone; Ethylene ketal; Monohydrolysis; Tosyl hydrazone

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPENTANONE; FUMARIC ACID DERIVATIVE; FUMARIC ACID DIETHYL ESTER;

ARTICLE; CHEMISTRY; HYDROLYSIS; SYNTHESIS;

CYCLOPENTANES; FUMARATES; HYDROLYSIS;

EID: 84856168011     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010001     Document Type: Article

References (21)

1. Braun, M.; Hirsch, A. Fullerene derivatives in bilayer membranes: An overview. Carbon 2000, 38, 1565-1572.
2. Taylor, R.; Walton, D.R.M. The chemistry of fullerenes. Nature 1993, 363, 685-693.
3. Sijbesma, R.; Srdanov, G.; Wudl, F.; Castoro, J.A.; Wilkins, C.; Friedman, S.H.; Decamp, D.L.; Kenyon, G.L. Synthesis of a fullerene derivative for the inhibition of HIV enzymes. J. Am. Chem. Soc. 1993, 115, 6510-6512. (Pubitemid 23276369)
4. Friedman, S.H.; Decamp, D.L.; Sijbesma, R.P.; Srdanov, G.; Wudl, F.; Kenyon, G.L. Inhibition of the HIV-1 protease by fullerene derivatives: Model building studies and experimental verification. J. Am. Chem. Soc. 1993, 115, 6506-6509. (Pubitemid 23276368)
5. Kotelnikova, R.A.; Kotelnikov, A.I.; Bogdanov, G.N.; Romanova, V.S.; Kuleshova, E.F.; Parnes Z.N.; Vol'pin, M.E. Membranotropic properties of the water soluble amino acid and peptide derivatives of fullerene C60. FEBS Lett. 1996, 389, 111-114. (Pubitemid 26226480)
6. An, Y.Z.; Chen, C.; Anderson, J.L.; Sigman, D.S.; Foote, C.S.; Rubin, Y.J. Sequence-specific modification of guanosine in DNA by a C60-linked deoxyoligonucleotide: Evidence for a non-singlet oxygen mechanism. Tetrahedron 1996, 52, 5179-5189.
7. Marchesan, S.; Da Ros, T.; Spalluto, G.; Balzarini, J.; Prato, M. Anti-HIV properties of cationic fullerene derivatives. Bioorg. Med. Chem. Lett. 2005, 15, 3615-3618. (Pubitemid 40942069)
8. Kotelnikova, R.A.; Bogdanov, G.N.; Frog, E.C.; Kotelnikov, A.I.; Shtolko, V.N.; Romanova, V.S.; Andreev, S.M.; Kushch, A.A.; Fedorova, N.E.; Medzhidova, A.A.; et al. Nanobionics of pharmacologically active derivatives of fullerene C60. J. Nanopart. Res. 2003, 5, 561-566.
9. Mroza, P.; Tegosa, G.P.; Galic, J.; Whartonc, T.; Sarnad, T.; Hamblin, M.R. Photodynamic therapy with fullerenes. Photochem. Photobiol. Sci. 2007, 6, 1139-1149. (Pubitemid 350064036)
10. Diedrich, F.; Isaacs, L.; Philip, D. Syntheses, structures, and properties of methanofullerenes. Chem. Soc. Rev. 1994, 23, 243-255.
11. Li, Z.; Bouhadir, K.H.; Shevlin, P.B. Convenient syntheses of 6,5-open and 6,6-closed cycloalkylidenefullerenes. Tetrahedron Lett. 1996, 37, 4651-4654. (Pubitemid 26225547)
12. Sample, T.E.; Hatch, L.F. Diethyl trans-delta4-tetrahydrophthalate. Org. Synth. 1970, 50, 43-49.
13. Giuliano, R.; Artico, M.; Nacci, V. Sarkomycin and analogous compounds. VII. New syntheses of cyclopentanone-3,4-dicarboxylic acid. Ann. Chim. 1961, 51, 491-498.
14. Auwers, K. Butanetetracarboxylic acid. Synthesis of pentamethylene derivatives. Ber. Dtsch. Chem. Ges. 1893, 26, 364-378.
15. Auwers, K.; Jacob, A. Stereoisomeric butanetetracarboxylic acids. Ber. Dtsch. Chem. Ges. 1894, 27, 1114-1132.
16. Huet, F.; Lechevallier, A.; Pellet, M.; Conia, J.M. Wet silica gel; a convenient reagent for deacetalization. Synthesis 1978, 63, 63-65.
17. Niwayama, S. Highly efficient selective monohydrolysis of symmetric diesters. J. Org. Chem. 2000, 65, 5834-5836.
18. Dahlgren, A.; Branalt, J.; Kvarnstrom, I.; Nilsson, I.; Musil, D.; Samuelsson, B. Synthesis of potential thrombin inhibitors. Incorporation of tartaric acid templates as P2 proline mimetics. Bioorg. Med. Chem. 2002, 10, 1567-1580. (Pubitemid 34214719)
19. Ishida, T.; Shinozuka, K.; Nogami, T.; Kubota, M.; Ohashi, M. Synthesis and characterization of C60 derivatives possessing TEMPO radicals. Tetrahedron 1996, 52, 5103-5112.
20. Oda, O.; Kojima, K.; Sakai, K. Synthesis of optically active (-)11-deoxy-11a-hydroxymethyl prostagladin E1. Tetrahedron Lett. 1975, 16, 3709-3712.
21. Rosenquist, A.; Kvarnstrom, I.; Svenson, S.C.T.; Classon, B.; Samuelsson, B. Synthesis of enantiomerically pure trans-3,4-substituted cyclopentanols by enzymic resolution. Acta Chem. Scan. 1992, 46, 1127-1129.