Preparation and improved stability of n-boc-α-amino-5-acyl meldrum's acids, a versatile class of building blocks for combinatorial chemistry

Journal of Combinatorial Chemistry

Volumn 4, Issue 5, 2002, Pages 470-474

  Raillard, Stephen P ^a,b   Chen, Weiwei ^a   Sullivan, Edward ^a   Bajjalieh, William ^a   Bhandari, Ashok ^a   Baer, Ted A ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

^b XenoPort Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0038897326     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0200033     Document Type: Article

References (18)

1. Bhandari, A.; Li, B.; Gallop, M. A. Solid-Phase Synthesis of Pyrrolo[3,4-b]pyridines and Related Pyridine-Fused Heterocycles. Synthesis 1999, 1951-1960.
2. Tadesse, S.; Bhandari, A.; Gallop, M. A. Solid-Phase Synthesis of Highly Functionalized 2,2'-Bipyridines. J. Comb. Chem. 1999, 1, 184-187.
3. Tietze, L. F.; Steinmetz, A.; Balkenhohl, F. Solid-Phase Synthesis of Polymer-Bound β-Ketoesters and Their Application in the Synthesis of Structurally Diverse Pyrazolones. Bioorg. Med. Chem. Lett. 1997, 7, 1303-1306.
4. Weber, L.; Iaiza, P.; Biringer, G.; Barbier, P. Solid Phase Synthesis of 3-Acyltetramic Acids. Synlett 1998, 1156-1158.
5. Oikawa, Y.; Sugano, K.; Yonemitsu, O. Meldrum's Acid in Organic Synthesis. 2. A General and Versatile Synthesis of β-Keto Esters. J. Org. Chem. 1978, 43, 2087-2088.
6. Maibaum, J.; Rich, D. Synthesis of the Novel π-(Benzyloxymethyl)-Protected Histidine Analogue of Statine. Inhibition of Penicillopepsin by Pepstatin-Derived Peptides Containing Different Statine Side-Chain Derivatives. J. Med. Chem. 1989, 32, 1571-1576.
7. Sorensen, U. S.; Falch, E.; Krogsgaard-Larsen, P. A Novel Route to 5-Substituted 3-Isoxazolols. Cyclization of N,O-DiBoc β-Keto Hydroxamic Acids Synthesized via Acyl Meldrum's Acids. J. Org. Chem. 2000, 65, 1003-1007.
8. Courcambeck, J.; Bihel, F.; De Michelis, C.; Quelever, G.; Kraus, J. L. Design of potential new HIV protease inhibitors: enantioconvergent synthesis of new pyrrolidin-3-ol, and pyrrolidin-3-one peptide conjugates. J. Chem. Soc., Perkin Trans. 2001, 1421-1430.
9. Li, B.; Franck, R. W. Facile Synthesis of N-Protected γ- and δ-Amino-β-keto-esters. Bioorg. Med. Chem. Lett. 1999, 2629-2634.
10. Houghton, R.; Lapham, D. J. A Modified Preparation of β-Keto Esters. Synthesis 1982, 451-452.
11. Smrcina, M.; Majer, P.; Majerova, E.; Guerassina, T. A.; Eissenstat, M. A. Facile Stereoselective Synthesis of γ-Substituted γ-Amino Acids from the Corresponding α-Amino Acids. Tetrahedron 1997, 53, 12867-12874.
12. Schmidt, H.-W.; Klade, M. A. Convenient Synthesis of β-Keto Diesters. Org. Prep. Proced. Int. 1988, 20, 184-187.
13. Oikawa, Y.; Yoshioka, T.; Sugano, K.; Yonemitsu, O. Methyl Phenylacetylacetate from Phenylacetyl Chloride and Meldrum's Acid. Org. Synth. 1985, 63, 359-361.
14. Rosowsky, A.; Forsch, R.; Uren, J.; Wick, M.; Kumar, M. M.; Freisheim, J. H. Methotrexate Analogues. 20. Replacement of Glutamate by Longer-Chain Amino Diacids: Effects on Dihydrofolate Reductase Inhibition, Cytotoxicity, and in Vivo Antitumor Activity. J. Med. Chem. 1983, 26, 1719-1724.
15. Hamada, Y.; Kondo, Y.; Shibata, M.; Shiori, T. Efficient Total Synthesis of Didemnins A and B. J. Am. Chem. Soc. 1989, 111, 669-673.
16. Ewing, W. R.; Joullie, M. M. A Short, Stereocontrolled Synthesis of (-)-Detroxinine. Heterocycles 1988, 27, 2843-2850.
17. Jouin, P.; Castro, B. Stereospecific Synthesis of N-Protected Statine and Its Analogues via Chiral Tetramic Acid. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182.
18. Dale, J. A.; Dull, D. L.; Mosher, H. S. α-Methoxy-α-trifluoromethylphenylacetic acid, a Versatile Reagent for the Determination of Enantiomeric Composition of Alcohols and Amines. J. Org. Chem. 1969, 34, 2543-2549.