An expedient synthesis of (+)-quinolactacin A2

Tetrahedron Letters

Volumn 45, Issue 48, 2004, Pages 8793-8795

  Park, Su Jin ^a   Cho, Kwang Nym ^a   Kim, Won Gon ^b   Lee, Kee In ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

ketoester; (+) Quinolactacin A2; Friedl nder type annulation; Isatoic anhydride

Indexed keywords

ESTER DERIVATIVE; ISOLEUCINE; QUINOLACTACIN A; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 7444249507     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.001     Document Type: Article

References (18)

1. N. Kakinuma, H. Iwai, S. Takahashi, K. Hamano, T. Yanagisawa, K. Nagai, K. Tanaka, K. Suzuki, F. Kirikae, T. Kirikae, and A. Nakagawa J. Antibiot. 53 2000 1247
2. S. Takahashi, N. Kakinuma, H. Iwai, T. Yanagisawa, K. Nagai, K. Suzuki, T. Tokunaga, and A. Nakagawa J. Antibiot. 53 2000 1252
3. W.-G. Kim, N.-K. Song, and I.-D. Yoo J. Antibiot. 54 2001 831
4. K. Tatsuta, H. Misawa, and K. Chikauchi J. Antibiot. 54 2001 109
5. X. Zhang, W. Jiang, and Z. Sui J. Org. Chem. 68 2003 4523
6. G.M. Coppola Synthesis 1980 505
7. G.M. Coppola, and G.E. Hardtmann J. Heterocycl. Chem. 16 1979 1605
8. Y. Hamada, Y. Kondo, M. Shibata, and T. Shioiri J. Am. Chem. Soc. 111 1989 669
9. B.D. Harris, and M.M. Joullié Tetrahedron 44 1988 3489
10. M.W. Rathke J. Am. Chem. Soc. 92 1970 3222
11. M. Paris, J.-A. Fehrentz, A. Heitz, A. Loffet, and Z. Martinez Tetrahedron Lett. 47 1996 8489
12. T. Shioiri, K. Hayashi, and Y. Hamada Tetrahedron 49 1993 1913
13. P.G. Dorma, K.K. Eng, R.N. Farr, G.R. Humphrey, J.C. McWilliams, P.J. Reider, J.W. Sager, and R.P. Volante J. Org. Chem. 68 2003 467
14. J.-L. Vasse, V. Levacher, J. Bourguignon, and G. Dupas Tetrahedron 59 2003 4911
15. P. Camps, E. Gómez, D. Muñoz-Torrero, and M. Arnó Tetrahedron: Asymmetry 12 2001 2909
16. 5: 416.2311, Found: 416.2309
17. 4]
18. 2O (45:50); flow rate, 1 mL/min; UV absorbance at 315 nm; retention time, (+)-quinolactacin A1 (9.8 min) and (+)-quinolactacin A2 (10.7 min). (+)-quinolactacin A1: [α] D 21 +10.8 (c 0.39, DMSO)