Y. K. Kang et al. / Bioorg. Med. Chem. Lett. 10 (2000) 95±99
99
References and Notes
(s, 2H), 5.13±5.20 (m, 1H), 5.23 (s, 2H), 7.52 (d, 2H, J=8.7
1
Hz), 8.25 (d, 2H, J=8.7 Hz). 19b: H NMR (CDCl3) d 1.03±
1. Shih, D. H.; Baker, F.; Cama, L.; Christensen, B. G. Het-
erocycles 1984, 21, 29.
2. Sunagawa, M.; Matsumura, H.; Inoue, T.; Fukasawa, M.;
Kato, M. J. Antibiot. 1990, 43, 519.
3. Yamaji, E.; Watanabe, T.; Nakayama, I. Abstracts of
Papers, H141, 35th Interscience Conference on Antimicrobial
Agents and Chemotherapy, San Francisco, CA, 17±20 Septem-
ber 1995.
4. Arakawa, S.; Kamidono, S.; Inamatsu, T.; Shimada, J.
Abstracts of Papers, F218, 37th Interscience Conference on
Antimicrobial Agents and Chemotherapy, Toronto, Ontario,
28 September±1 October 1997.
5. Pelak, B. A.; Gerckens, L. S.; Scott, P. M.; Gill, C.; Pacho-
lok, C.; Lynch, L.; Dorso, K.; Kohler, J.; Shungu, D.; Rosen,
H.; Kroppe, H. Abstracts of Papers, F119, 36th Interscience
Conference on Antimicrobial Agents and Chemotherapy, New
Orleans, LA, 15±18 September 1996.
6. Sato, N.; Sasho, M.; Kamada, A.; Suzuki, T.; Ashizawa, K.;
Sugiyama, I. Abstracts of Papers, F151, 35th Interscience
Conference on Antimicrobial Agents and Chemotherapy, San
Francisco, CA, 17±20 September 1995.
7. Tawara, S.; Matsumoto, S.; Matsumoto, Y.; Ishiguro, K.;
Maki, K.; Sasaki, K.; Matsuda, K. Abstracts of Papers, F145,
35th Interscience Conference on Antimicrobial Agents and
Chemotherapy, San Francisco, CA, 17±20 September 1995.
8. Shin, K. J.; Yoo, K. H.; Kim, D. J.; Park, S. W.; Ko, B. S.;
Lee, S. J.; Huh, J. D.; Park, S. Y. Bioorg. Med. Chem. Lett.
1998, 8, 1607.
1.85 (m, 1H), 2.33 (s, 3H), 2.38±2.46 (m, 1H), 2.52±2.62 (m,
1H), 2.99±3.05 (m, 1H), 3.15±3.22 (m, 2H), 3.76±3.82 (m, 1H),
4.26 (d, 4H), 4.26 (s, 2H), 4.89±4.96 (m, 1H), 5.21 (s, 2H), 7.52
(d, 2H, J=8.2 Hz), 8.23 (d, 2H, J=8.2 Hz). 26: 1H NMR
(CDCl3) d 2.01±2.11 (m, 1H), 2.20±2.30 (m, 1H), 2.32 (s, 3H),
2.80±2.92 (m, 1H), 3.40±3.48 (m, 1H), 4.00±4.12 (m, 1H),
4.13±4.24 (m, 1H), 4.70 (s, 2H), 5.20±5.31 (m, 2H), 6.19 (s,
1H), 7.26 (d, 1H, J=7.6 Hz), 7.50 (d, 1H, J=7.6 Hz), 8.12 (d,
1H, J=7.6 Hz), 8.21 (d, 1H, J=7.6 Hz).
14. Mitsunobu, O. Synthesis 1981, 1.
15. Kumagai, T.; Abe, T.; Fujimoto, Y.; Hayashi, T.; Inoue,
Y.; Nagao, Y. Heterocycles 1993, 36, 1729.
1
16. 1a: H NMR (D2O) d 1.26 (d, 3H, J=7.1 Hz, b-methyl),
1.32 (d, 3H, J=6.3 Hz, CH3CHOH), 1.82±1.85 (m, 1H), 2.51±
2.62 (m, 1H), 2.71 (s, 3H), 2.91±3.02 (m, 1H), 3.25±3.28 (m,
1H), 3.32±3.49 (m, 1H), 3.51±3.61 (m, 1H), 3.68±3.92 (m, 1H),
3.91±4.01 (m, 1H), 4.21±4.33 (m, 2H), 4.58±4.66 (m, 1H);
FABHRMS m/z calcd for C18H28N3O5S (M+H)+ 398.1750,
found 398.1745. 1b: 1H NMR (D2O) d 1.27 (d, 3H, J=7.1
Hz, b-methyl), 1.36 (d, 3H, J=6.3 Hz, CH3CHOH), 1.50±1.61
(m, 1H), 1.80±1.98 (m, 1H), 2.02±2.18 (m, 1H), 2.51±2.63 (m,
1H), 2.98 (s, 3H), 3.14±3.22 (m, 1H), 3.26±3.34 (m, 1H), 3.44±
3.61 (m, 3H), 3.70 (s, 3H), 3.82±3.96 (m, 1H), 4.21±4.33 (m,
1
2H). 1c: H NMR (D2O) d 1.23 (d, 3H, J=7.1 Hz, b-methyl),
1.30 (d, 3H, J=6.3 Hz, CH3CHOH), 1.62±1.68 (m, 1H), 1.82±
1.85 (m, 1H), 2.38±2.43 (m, 1H), 2.71 (s, 3H), 3.03±3.12 (m,
1H), 3.29±3.41 (m, 4H), 3.42±3.55 (m, 2H), 3.89±3.99 (m, 1H),
1
4.21±4.33 (m, 2H). 1d: H NMR (D2O) d 1.09 (d, 3H, J=6.9
9. Hwang, S. H.; Shin, K. J.; Kang, Y. K.; Kim, D. J.; Kim,
D. C.; Yoo, K. H.; Park, S. W.; Lee, K. J. Arch. Pharm.
Pharm. Med. Chem. 1998, 331, 139.
10. Kang, Y. K.; Shin, K. J.; Yoo, K. H.; Seo, K. J.; Park, S. Y.;
Kim, D. J.; Park, S. W. Bioorg. Med. Chem. Lett. 1999, 9, 2385.
11. Nishi, K.; Imuta, M.; Kimura, Y.; Miwa, H. J. Antibiot.
1995, 48, 1481.
Hz, b-methyl), 1.24 (d, 3H, J=6.3 Hz, CH3CHOH), 1.28±1.38
(m, 1H), 2.30±2.42 (m, 1H), 2.76±2.82 (m, 1H), 3.02±3.18 (m,
1H), 3.21±3.34 (m, 1H), 3.33±3.40 (m, 3H), 3.41±3.52 (m, 1H),
3.60±3.70 (m, 1H), 3.76 (s, 3H). 4.02±4.18 (m, 2H), 4.90±4.98
(m, 1H). 1e: 1H NMR (D2O) d 1.05 (d, 3H, J=7.0 Hz, b-
methyl), 1.12 (d, 3H, J=6.2 Hz, CH3CHOH), 1.34±1.52 (m,
1H), 2.34±2.52 (m, 1H), 2.74±2.92 (m, 1H), 3.01±3.10 (m, 1H),
3.25±3.32 (m, 3H), 3.33±3.42 (m, 1H), 3.55±3.69 (m, 1H),
3.75±3.86 (m, 1H). 4.01±4.12 (m, 2H), 4.23 (s, 2H), 4.91±5.02
(m, 1H). 1f: 1H NMR (D2O) d 1.10 (d, 3H, J=7.1 Hz, b-
methyl), 1.18 (d, 3H, J=6.3 Hz, CH3CHOH), 1.32±1.42 (m,
1H), 2.32±2.46 (m, 1H), 2.80±2.96 (m, 2H), 3.10±3.34 (m, 4H),
3.56±3.62 (m, 3H), 4.07±4.15 (m, 2H), 4.27 (s, 2H);
FABHRMS m/z calcd for C18H26N3O6S (M+H)+ 412.1543,
found 412.1527. 1g: 1H NMR (D2O) d 1.09 (d, 3H, J=7.3 Hz,
b-methyl), 1.15 (d, 3H, J=6.3 Hz, CH3CHOH), 1.60±1.76 (m,
1H), 1.77±1.89 (m, 1H), 2.52±2.70 (m, 1H), 2.82±2.91 (m, 1H),
3.14±3.20 (m, 1H), 3.21±3.26 (m, 1H), 3.66±3.80 (m, 1H),
4.08±4.17 (m, 1H), 4.18±4.30 (m, 1H), 4.61 (s, 2H), 6.38 (s,
1H); FABHRMS m/z calcd for C18H24N3O6S (M+H)+
410.1387, found 410.1390.
12. Burton, G.; Clarke, G. J.; Douglas, J. D.; Eglington, A. J.;
Frydrych, C. H.; Hinks, J. D.; Hird, N. W.; Moss, S. F.;
Naylor, A.; Nicholson, N. H.; Pearson, M. J. J. Antibiot. 1996,
49, 1266.
1
13. 11a: H NMR (CDCl3) d 1.19±2.19 (m, 1H), 2.26 (s, 3H),
2.33±2.46 (m, 2H), 2.56±2.73 (m, 4H), 3.10±3.15 (m, 1H),
3.24±3.32 (m, 1H), 3.70±3.78 (m, 1H), 4.01±4.08 (m, 2H),
4.13±4.23 (m, 1H), 4.66±4.74 (m, 1H), 5.13 (s, 2H), 7.46 (d,
2H, J=8.6 Hz), 8.15 (d, 2H, J=8.6 Hz). 16a: 1H NMR
(CDCl3) d 1.36 (t, 3H), 1.74±1.77 (m, 1H), 2.33 (s, 3H), 2.30±
2.47 (m, 1H), 2.84±3.12 (m, 1H), 3.12±3.46 (m, 2H), 3.80±3.88
(m, 1H), 4.03±4.18 (m, 2H), 4.34 (d, 2H), 5.22 (s, 2H), 5.28±
5.42 (m, 1H), 7.52 (d, 2H, J=8.8 Hz), 8.23 (d, 2H, J=8.8 Hz).
19a: 1H NMR (CDCl3) d 1.83±1.90 (m, 1H), 2.35 (s, 3H),
2.36±2.48 (m, 1H), 2.82±2.92 (m, 1H), 3.14±3.28 (m, 2H),
3.84±3.90 (m, 1H), 4.06±4.12 (m, 1H), 4.14±4.18 (m, 1H), 4.46
17. Ohtake, N.; Yamada, K.; Mano, E.; Okamoto, O.; Ush-
ijima, R.; Nakagawa, S. J. Antibiot. 1995, 50, 567.