Synthesis of proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3233-3236

  Tao, Junhua ^a,b   Hu, Shanghui ^b   Pacholec, Michelle ^a   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; COUMARIN;

ARTICLE; CYCLIZATION; DECOMPOSITION; DEPROTECTION REACTION; DRUG SYNTHESIS; EPIMERIZATION; METHYLATION; OXIDATION;

ANTI-BACTERIAL AGENTS; CATALYSIS; COUMARINS; CYCLIZATION; ENDOPEPTIDASES; ESTERASES; KETO ACIDS; KINETICS; LIPASE; METHYLATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0141632774     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035101r     Document Type: Article

References (17)

1. (a) Maxwell, A. Trends Microbiol. 1997, 5, 102.
2. (b) Calia, H.; Hoerman, L.; Schultz, P.; Lebeau, L.; Mallouh, V.; Wigley, D. B.; Wang, J. C.; Mioskowski, C.; Oudet, P. J. Mol. Biol. 1994, 236, 618.
3. Boehm, H. J.; Boehringer, M.; Bur, D.; Gmeunder, H.; Huber, W.; Klaus, W.; Kostrewa, D.; Kuehne, H.; Luebbers, T.; Meunier-Keller, N.; Mueller, F. J. Med. Chem. 2000, 43, 2664.
4. Chen, H.; Walsh, C. T. Chem. Biol. 2001, 8, 301.
5. Marahiel, M.; Stachelhaus, T.; Mootz, H. D. Chem. Rev. 1997, 97, 2651.
6. For representative syntheses of thioesters with no amino groups: (a) Cheung, K.-M.; Coles, S. J.; Hursthouse, M. B.; Johnson, N. J.; Shoolingin-Jordan, P. M. Angew. Chem., Int. Ed. 2001, 41, 1199. (b) Hunziker, D.; Wu, N.; Kenoshita, K.; Cane, D. E.; Khosla, C. Tetrahedron Lett. 1999, 40, 635.
7. For representative syntheses of thioesters with no amino groups: (a) Cheung, K.-M.; Coles, S. J.; Hursthouse, M. B.; Johnson, N. J.; Shoolingin-Jordan, P. M. Angew. Chem., Int. Ed. 2001, 41, 1199. (b) Hunziker, D.; Wu, N.; Kenoshita, K.; Cane, D. E.; Khosla, C. Tetrahedron Lett. 1999, 40, 635.
8. Krysan, D. J. Tetrahedron Lett. 1996, 37, 3303.
9. Yazbeck, D. R.; Tao, J.; Martinez, C. A.; Kline, B. J.; Hu, S. Adv. Synth. Catal. 2003, 345, 524-532.
10. For enzymatic reduction on similar substrates, see: (a) Fadnavis, N. W.; Vadivel, S. K.; Sharfuddin, M.; Bhalerao, U. T. Tetrahedron: Asymmetry 1997, 8, 4003. (b) Dillon, M. P.; Hayes, M. A.; Simpson, T. J.; Sweeney, J. B. Biorg. Med. Chem. Lett. 1991, 1, 223.
11. For enzymatic reduction on similar substrates, see: (a) Fadnavis, N. W.; Vadivel, S. K.; Sharfuddin, M.; Bhalerao, U. T. Tetrahedron: Asymmetry 1997, 8, 4003. (b) Dillon, M. P.; Hayes, M. A.; Simpson, T. J.; Sweeney, J. B. Biorg. Med. Chem. Lett. 1991, 1, 223.
12. (a) Dong, L.; Miller, M. J. J. Org. Chem. 2002, 67, 4759.
13. (b) Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507.
14. For some recent applications of enzymatic resolution, see: (a) Demir, A. S.; Sesenoglu, O. Org. Lett. 2002, 4, 2021. (b) Taber, D. F.; Xu, M.; Hartnett, J. C. J. Am. Chem. Soc. 2002, 124, 13121. (c) Delhaes, L.; Biot, C.; Berry, L.; Delcourt, P.; Maciejewski, L. A.; Camus, D.; Brocard, J. S.; Dive, D. ChemBiochem 2002, 3, 418. (d) Luna, A.; Gotor, V. Org. Lett. 2002, 4, 3627.
15. For some recent applications of enzymatic resolution, see: (a) Demir, A. S.; Sesenoglu, O. Org. Lett. 2002, 4, 2021. (b) Taber, D. F.; Xu, M.; Hartnett, J. C. J. Am. Chem. Soc. 2002, 124, 13121. (c) Delhaes, L.; Biot, C.; Berry, L.; Delcourt, P.; Maciejewski, L. A.; Camus, D.; Brocard, J. S.; Dive, D. ChemBiochem 2002, 3, 418. (d) Luna, A.; Gotor, V. Org. Lett. 2002, 4, 3627.
16. For some recent applications of enzymatic resolution, see: (a) Demir, A. S.; Sesenoglu, O. Org. Lett. 2002, 4, 2021. (b) Taber, D. F.; Xu, M.; Hartnett, J. C. J. Am. Chem. Soc. 2002, 124, 13121. (c) Delhaes, L.; Biot, C.; Berry, L.; Delcourt, P.; Maciejewski, L. A.; Camus, D.; Brocard, J. S.; Dive, D. ChemBiochem 2002, 3, 418. (d) Luna, A.; Gotor, V. Org. Lett. 2002, 4, 3627.
17. For some recent applications of enzymatic resolution, see: (a) Demir, A. S.; Sesenoglu, O. Org. Lett. 2002, 4, 2021. (b) Taber, D. F.; Xu, M.; Hartnett, J. C. J. Am. Chem. Soc. 2002, 124, 13121. (c) Delhaes, L.; Biot, C.; Berry, L.; Delcourt, P.; Maciejewski, L. A.; Camus, D.; Brocard, J. S.; Dive, D. ChemBiochem 2002, 3, 418. (d) Luna, A.; Gotor, V. Org. Lett. 2002, 4, 3627.