Synthesis of Dimethyl Sulfomycinamate

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4421-4424

  Bagley, Mark C ^a   Dale, James W ^a   Xiong, Xin ^a   Bower, Justin ^b  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b Vernalis PLC   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; DIMETHYL SULFOMYCINAMATE; OXAZOLE; PYRIDINE; THIAZOLE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DEPROTECTION REACTION; DRUG SYNTHESIS; MICHAEL ADDITION; ROOM TEMPERATURE;

EID: 0344927874     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0357144     Document Type: Article

References (22)

1. Egawa, Y.; Umino, K.; Tamura, Y.; Shimizu, M.; Kaneko, K.; Sakurazawa, M.; Awataguchi, S.; Okuda, T. J. Antibiot. 1969, 22, 12.
2. Abe, H.; Kushida, K.; Shiobara, Y.; Kodama, M. Tetrahedron Lett. 1988, 29, 1401.
3. Konno, J.; Kameda, N.; Nishio, M.; Kinumaki, A.; Komatsubara, S. J. Antibiot. 1996, 49, 1063.
4. Abe, H.; Takaishi, T.; Okuda, T. Tetrahedron Lett. 1978, 2791.
5. Boeck, L. D.; Favret, M. E.; Wetzel, R. W. J. Antibiot. 1992, 45, 1278.
6. Liesch, J. M.; Rinehart, K. L., Jr. J. Am. Chem. Soc. 1977, 99, 1645.
7. Lau, R. C. M.; Rinehart, K. L., Jr. J. Antibiot. 1994, 47, 1467.
8. Yun, B.-S.; Hidaka, T.; Furihata, K.; Seto, H. J. Antibiot. 1994, 47, 969.
9. Kumar, E. K. S. V.; Kenia, J.; Mukhopadhyay, T.; Nadkarni, S. R. J. Nat. Prod. 1999, 62, 1562.
10. Yun, B.-S.; Seto, H. Biosci. Biotech. Biochem. 1995, 59, 876.
11. Yun, B.-S.; Hidaka, T.; Furihata, K.; Seto, H. J. Antibiot. 1994, 47, 510.
12. Rodriguez, J. C.; González Holgado, G.; Santamaria Sánchez, R. I.; Canedo, L. M. J. Antibiot. 2002, 55, 391.
13. Yun, B.-S.; Hidaka, T.; Furihata, K.; Seto, H. J. Antibiot. 1994, 47, 1541.
14. Yun, B.-S.; Hidaka, T.; Furihata, K.; Seto, H. Tetrahedron 1994, 50, 11659.
15. Matsumoto, M.; Kawamura, Y.; Yasuda, Y.; Tanimoto, T.; Matsumoto, K.; Yoshida, T.; Shoji, J. J. Antiobiot. 1989, 42, 1465.
16. Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623.
17. Bohlmann, F.; Rahtz, D. Chem. Ber. 1957, 90, 2265.
18. Bagley, M. C.; Dale, J. W.; Bower, J. Synlett 2001, 1149.
19. 4 followed by reaction with 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl).
20. Baraldi, P. G.; Simoni, D.; Manfredini, S. Synthesis 1983, 902.
21. Bagley, M. C.; Brace, C.; Dale, J. W.; Ohnesorge, M.; Phillips, N. G.; Xiong, X.; Bower, J. J. Chem. Soc., Perkin Trans, 1 2002, 1663.
22. Kim, H.-O.; Olsen, R. K.; Choi, O.-S. J. Org. Chem. 1987, 52, 4531.