Total synthesis of antibiotic, micrococcin P, from 2,3,6-polythiazolesubstituted pyridine skeleton [fragment A-C]

Chemistry Letters

Volumn , Issue 2, 1998, Pages 139-140

  Shin, Chung gi ^a   Okumura, Kazuo ^a   Shigekuni, Masashi ^a   Nakamura, Yutaka ^a  

^a KANAGAWA UNIVERSITY   (Japan)

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Indexed keywords

EID: 0032387024     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.139     Document Type: Article

References (14)

1. a) P. Valente, R. Rabanal, and G. Lukacs, J. Chem. Soc., Chem. Commun., 1977, 706,
2. b) B. W. Bycroft and M. S. Gowland, J. Chem. Soc., Chem. Commun., 1978, 256.
3. For examples: M. Debono, R. M. Molly, J. L. Occlowitz, J. W. Paschel, A. H. Hunt, K. H. Michel, and J. W. Martin, J. Org. Chem., 57, 5200 (1988).; H. Abe, K. Kushida, Y. Shiobara, and M. Kodama, Tetrahedron Lett., 29, 1401 (1988).
4. For examples: M. Debono, R. M. Molly, J. L. Occlowitz, J. W. Paschel, A. H. Hunt, K. H. Michel, and J. W. Martin, J. Org. Chem., 57, 5200 (1988).; H. Abe, K. Kushida, Y. Shiobara, and M. Kodama, Tetrahedron Lett., 29, 1401 (1988).
5. K. Okumura, M. Shigekuni, Y. Nakamura, and C. Shin, Chem. Lett., 1996, 1025.
6. a) Y. Nakamura, C. Shin, K. Umemura, and J. Yoshimura, Chem. Lett., 1992, 1005,
7. b) C. Shin, Y. Nakamura, Y. Yamada, Y. Yonezawa, K. Umemura, and J. Yoshimura, Bull. Chem. Soc. Jpn., 68, 3151 (1995).
8. BOP: Benzotriazole-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate.
9. 2), 5.90 (br d, 1H, NH, J=8.3 Hz), 6.85-7.00 (m, 1H, NH), 7.35 (s, 5H, Ph).
10. 2 x 2), 5.15 (s, 2H, Cbz's CH), 5.76 (br d, 1H, NH, J=6.6 Hz), 6.90-7.00 (m, 1H, NH), 7.37 (s, 5H, Ph).
11. 3CW=, J=7.3 Hz), 7.26-7.77 (m, 10H, Ph x 2), 8.05 (s, 1H, Thiazole ring-H), 8.37 (br s, 1H, NH).
12. 3CH =), 7.66 (br d, 1H, BocNH, J=7.9 Hz), 7.90-8.55 (m, 9H, Thiazole ring-H x 5, Pyridine ring-H x 2, and NH x 2), 9.82 (s, 1H, COOH).
13. 3CH= x 2, J=7.3 Hz), 7.31-7.33 (m, 11H, TPS' Ph x 2, NH), 8.02 (br d, 1H, NH, J=8.5 Hz), 8.17-8.31 (m, 5H, NH x 2, Thiazole ring-H x 2, Pyridine ring-H), 8.38, 8.43 and 8.47 (each s, 3H, Thiazole ring-H x 3), 8.48 (d, 1H, Pyridine ring-H, J=8.3 Hz), 9.84 and 9,92 (each br s, 2H, NH x 2).
14. 6) δ=13.4, 13.8, 18.6, 19.7, 19.9, 20.1, 20.4, 31.8, 46.4, 55.8, 58.1, 58.8, 65.0, 66.6, 66.7, 118.4, 121.8, 122.0, 123.9, 125.1, 125.4, 126.0, 127.2, 128.2, 129.8, 129.9, 131.5, 140.8, 148.4, 148.6, 148.7, 149.1, 149.7, 150.2, 150.4, 152.2, 158.8, 160.0, 160,4, 160.4, 161.7, 163.7, 166.2, 166.5, 168.4, 168.8, 169.6, 170.6.