Syntheses of 5- and 6-[2,3]-dihydrobenzofuran β-amino acids

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5803-5806

  Coleman, Paul J ^a   Hutchinson, John H ^a   Hunt, Cecilia A ^a   Lu, Ping ^a   Delaporte, Enock ^a   Rushmore, Tom ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ASPARTIC ACID; BENZOFURAN DERIVATIVE; BETA AMINO ACID; CYTOCHROME P450;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL STRUCTURE; ENZYME INDUCTION; ENZYME INHIBITION; MOLECULAR MIMICRY; STEREOCHEMISTRY;

EID: 0034729971     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00965-5     Document Type: Article

References (15)

1. Duggan, M. E.; Hartman, G. D.; Hoffman, W. F.; Meissner, R. S.; Perkins, J. J.; Askew, B. C.; Coleman, P. J.; Hutchinson, J. H.; Naylor-Olsen, A. D. US Patent 5,981,546, 9 November 1999.
2. (a) Zablocki, J. A.; Rico, J. G.; Garland, R. B.; Rogers, T. E.; Williams, K.; Schretzman, L. A.; Rao, S. A.; Bovy, P. R.; Tjoeng, F. S.; Lindmark, R. J.; Toth, M. V.; Zupec, M. E.; McMackins, D. E.; Adams, S. P.; Miyano, M.; Markos, C. S.; Milton, M. N.; Paulson, S.; Herin, M.; Jacqmin, P.; Nicholson, N. S.; Panzer-Knodle, S. G.; Haas, N. F.; Page, J. D.; Szalony, J. A.; Taite, B. B.; Salyers, A. K.; King, L. W.; Campion, J. G.; Feigen, L. P. J. Med. Chem. 1995, 38, 2378-2394.
3. (b) Stilz, H. U.; Jablonka, B.; Just, M.; Knolle, J.; Paulus, E. F.; Zoller, G. J. Med. Chem. 1996, 39, 2118-2122.
4. (c) Hoekstra, W. J.; Maryanoff, B. E.; Andrade-Gordon, P.; Cohen, J. H.; Constanzo, M. J.; Damiano, B. P.; Haertlein, B. J.; Harris, B. D.; Kauffman, J. A.; Keane, P. M.; McComsey, D. F.; Villani, F. J.; Yabut, S. C. Bioorg. Med. Chem. Lett. 1996, 6, 2371-2376.
5. (a) Wilkinson, C. F.; Murray, M.; Marcus, C.; Dube, C. In Pestic. Chem.: Hum. Welfare Environ., Proc. 5th Int. Congr. Pestic. Chem., Meeting Date 1982; Miyamoto, J.; Kearney, P. C., Eds.; Dept. Entomol., Cornell Univ., Ithaca, NY, USA. Pergamon: Oxford, 1983; Vol. 3, pp. 463-468.
6. (b) Dahl, A. R.; Brezinski, D. A. Inhal. Toxicol. Res. Inst., Albuquerque, NM, USA. Biochem. Pharmacol. 1985, 34(5), 631-636.
7. (a) Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183.
8. (b) Davies, S. G.; Garrido, N. M.; Ichihara, O.; Walters, I. A. S. J. Chem. Soc., Chem. Commun. 1993, 1153.
9. Barker, P.; Finke, P.; Thompson, K. Synth. Commun. 1989, 19, 257-265.
10. Available from Lancaster Synthesis.
11. Silylation of the phenolic oxygen in 8 allows dissolution of 9 in organic solvents. Without protection, the metal alkoxide derived from deprotonation of 8 is highly insoluble.
12. The stereoassignment of 12 as the (S)-diastereomer is based on the Davies precedent (see Ref. 3).
13. 1H NMR (300 MHz, MeOD) δ 7.27 (d, J=7.5 Hz, 1H), 6.89 (dd, J=7.5, 1.8 Hz, 1H), 6.84 (d, J=1.8 Hz, 1H), 4.59 (m, 3H), 4.15 (q, J=7.5 Hz, 2H), 3.20 (t, J=8.4 Hz, 2H), 2.99 (m, 2H), 1.21 (t, J=7.5 Hz, 3H) ppm.
14. 1H NMR (300 MHz, MeOD) δ 7.29 (s, 1H), 7.14 (dd, J=8.1, 1.5 Hz, 1H), 6.73 (d, J=8.1 Hz, lH), 4.55 (t, J=8.7 Hz, 2H), 4.52 (m, 1H), 4.12 (q, J=7.5 Hz, 2H), 3.24 (t, J=8.7 Hz, 2H), 2.92 (m, 2H), 1.19 (t, J=7.5 Hz, 3H) ppm.
15. ®).