Solid-phase synthesis of optically active substituted 2-aminofuranones using an activated carbonate linker

Molecules

Volumn 14, Issue 10, 2009, Pages 3914-3921

  Matiadis, Dimitris ^a   Prousis, Kyriakos C ^a   Igglessi Markopoulou, Olga ^a  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

2 aminofuranones; Acylations; Heterocycles; Lactones; Solid phase synthesis

Indexed keywords

CARBONIC ACID DERIVATIVE; FURAN DERIVATIVE; HYDROXYACID; POLYSTYRENE DERIVATIVE; WANG RESIN;

ACYLATION; ARTICLE; CHEMISTRY; SYNTHESIS;

ACYLATION; CARBONATES; FURANS; HYDROXY ACIDS; POLYSTYRENES;

EID: 70350490221     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14103914     Document Type: Article

References (27)

1. Merrifield, R.B. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963, 85, 2149-2154.
2. Krchnak, V.; Holladay, M.W. Solid phase heterocyclic chemistry. Chem. Rev. 2002, 102, 61-91.
3. Nefzi, A.; Ostresh, J.M.; Houghten, R.A. The Current Status of Heterocyclic Combinatorial Libraries. Chem. Rev. 1997, 97, 449-472.
4. Franzen, R.G. Recent advances in the preparation of heterocycles on solid support: a review of the literature. J. Comb. Chem. 2000, 195-214.
5. Brown, A.R.; Hermkerns, P.H.H.; Ottenheijm, H.C.J.; Rees, D.C. Solid phase synthesis. Synlett 1998, 817-827.
6. Ganesan, A. In Methods in Enzymology, Vol. 369: Combinatorial Chemistry, Part B; Morales G.A., Bunin, B.A., Eds.; Elsevier: San Diego, CA, USA, 2003; pp. 415-434.
7. Pernerstorfer, J. In Combinatorial Chemistry: From Theory to Application; Bannwarth, W., Hinzen, B. Eds.; Wiley-VCH: Weinheim, Germany, 2006; pp. 111-142.
8. Jung, N.; Wiehn, M.; Braese S.; Multifunctional Linkers for Combinatorial Solid Phase Synthesis. Top. Curr. Chem. 2007, 278, 1-88.
9. Scott, P.J.H.; Steel, P.G. Diversity Linker Units for Solid Phase Organic Synthesis. Eur. J. Org. Chem. 2006, 2251-2268.
10. Tersteegen, A.; Heimbach, D.; Thede, K.; Welker, R.; Fast, B.; Paessens, A.; Dittmer, F.; Schohe- Loop, R.; Harrenga, A.; Hillisch, A.; Henninger, K.; Huebsch, W.; Bauser, M.; Greschat S.; Schneider, D.; Marquardt, T.; Goeller, A.; Urban, A.; Wildum, S.; Paulsen, D. Preparation of aminofuranones as HIV-1 protease inhibitors. WO 2008071359, 2008.
11. Buehler H.; Bayer A.; Effenberger F. A convenient synthesis of optically active 5,5-disubstituted 4-amino- and 4-hydroxy-2(5H)-furanones from (S)-ketone cyanohydrins. Chem. Eur. J. 2000, 2564-2571.
12. Menta, E.; Pescalli, N.; Conti, M.; Zimmerman, G. Ureido and thioureido derivatives of 4-amino- 2(5H)-furanones and 4-amino-2(5H)-thiophenones as antitumor agents. US Patent 6333346, 2001.
13. Hiyama T.; Oishi, H.; Suetsugu Y.; Nishide K.; Saimoto H. Synthesis of 4-amino-2(5H)-furanones through intra- and intermolecular nitrile addition of ester enolates. Construction of carbon framework of an antitumor antibiotic basidalin. Bull. Chem. Soc. Jpn. 1987, 60, 2139-2150.
14. Lattmann, E.; Dunn, S.; Niamsanit, S.; Sattayasai, N. Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones. Bioorg. Med. Chem. Lett. 2005, 15, 919-921.
15. Mavrov, M.; Simirskaya, N. Synthesis of substituted 3-aminospiro-4-but-2- enolides. Chem. Heter. Comp. 2000, 35, 1150-1155.
16. Pevet, I.; Meyer, C.; Cossy, J. [2,3]-Wittig sigmatropic rearrangement of γ-allyloxy-β-enaminoesters. Synlett 2003, 5, 663-666.
17. Hiyama, T.; Oishi, H.; Saimoto, H. New synthetic methods for 4-amino-2(5H)-furanones. Tetrahedron Lett. 1985, 26, 2459-2462.
18. Chiacchio, U.; Corsaro, A.; Iannazzo, D.; Piperno, A.; Procopio, A.; Rescifina, A.; Romeo, G.; Romeo, R. Intramolecular cycloadditions of alpha-allyloxycarbonylnitrones: Stereoselective synthesis of 3-amino-2(5H)furanones. J. Org. Chem. 2002, 67, 4380-4383.
19. Sandmann, G.; Ward, C.E.; Lo, W.C.; Nagy, J.O.; Boeger, P. Bleaching herbicide flurtamone interferes with phytoene desaturase. Plant Physiol. 1990, 94, 476-478.
20. Ward, C.E.; Lo, W.C.; Pomidor, P.B.; Tisdell, F.E.; Ho, A.W.W.; Chiu, C.L.; Tuck, D.M.; Bernando, C.R.; Fong, P.J.; Omid, A.; Buteau, F.A. 5-Aminofuran-3(2H)-ones. A new development in bleaching herbicides. In Synthesis and Chemistry of Agrochemicals; ACS Symposium Series, No. 35; Baker D.R., Fenyes J.G., Moberg W.K., Barrington, C., Eds.; American Chemical Society: Washington, DC, USA, 1987; pp. 65-73.
21. Athanasellis, G.; Detsi, A.; Prousis, K.C.; Igglessi-Markopoulou, O. Novel access to 2-aminofuranones via cyclization of functionalized γ-hydroxy-α, β-butenoates derived from Nhydroxybenzotriazole esters of α-hydroxy acids. Synthesis 2003, 2015-2022.
22. Athanasellis, G.; Gavrielatos, E.; Igglessi-Markopoulou, O. One-pot synthesis of optically active tetramic acids from amino acids mediated by 1-hydroxybenzotriazole. Synlett 2001, 10, 1653-1655.
23. Kikionis, S.; McKee, V.; Markopoulos, J.; Igglessi-Markopoulou, O. Regioselective ring opening of thiomalic acid anhydrides by carbon nucleophiles. Synthesis and X-ray structure elucidation of novel thiophenone derivatives. Tetrahedron 2009, 65, 3711-3716.
24. Mitsos C.A.; Zografos, A.L.; Igglessi-Markopoulou, O. Regioselective Ring Opening of Malic Acid Anhydrides by Carbon Nucleophiles. Application in the Synthesis of Chiral Tetronic Acids. J. Org. Chem. 2000, 65, 5852-5853.
25. Prousis, K.; Detsi, A.; Igglessi-Markopoulou O. A traceless solid-phase approach to functionalized tetramic acids and 2-amino-4-pyrrolinones. Synlett 2005, 18, 2763-2766.
26. Dressman, B.A.; Spangle, L.A.; Kaldor, S.W. Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization / cleavage step.Tetrahedron Lett. 1996, 37, 937-940.
27. Anschuetz, R. Imidotetronic acid. Ber. Dtsch. Chem. Ges. 1912, 2374-2378.