Stereochemistry of iejimalide B

Tetrahedron Letters

Volumn 44, Issue 7, 2003, Pages 1395-1399

  Tsuda, Masashi ^a   Nozawa, Kohei ^a   Shimbo, Kazutaka ^a   Ishiyama, Haruaki ^a   Fukushi, Eri ^a   Kawabata, Jun ^a   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Absolute configuration; Macrolide; Tunicate

Indexed keywords

IEJIMALIDE B; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EUDISTOMA;

EID: 0037429091     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02869-1     Document Type: Article

References (17)

1. Kobayashi J., Cheng J.-f., Ohta T., Nakamura H., Nozoe S., Hirata Y., Ohizumi Y., Sasaki T. J. Org. Chem. 53:1988;6147-6150.
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3. Cottard M., Kann N., Rein T., Åkermark B., Helquist P. Tetrahedron Lett. 36:1995;3115-3118.
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5. Iejimalides are found to show antitumor activity in vivo, unpublished data.
6. Shimbo K., Tsuda M., Fukushi E., Kawabata J., Kobayashi J. Tetrahedron. 56:2000;7923-7926.
7. Tsuda, M.; Nozawa, K.; Shimbo, K.; Kobayashi, J. J. Nat. Prod., in press.
8. 1H coupling constants for 1 (H/H): 3/4: 10.3, 4/5: 9.0, 4/43: 6.6, 5/6: 15.5, 8/9: 9.4, 9/10a: 2.7, 9/10b: 10.2, 10a/11: 4.7, 10b/11: 10.2, 11/12: 15.8, 14/15a: 11.1, 14/15b: 4.6, 15a/15b: 15.3, 15a/16a: 2.3, 15a/16b: 11.2, 15b/16a: 2.0, 15b/16b: 3.0, 16a/16b: 14.2, 16a/17: 10.0, 16b/17: 3.0, 17/18: 8.2, 18/19: 14.7, 19/20: 9.8, 20/21: 14.5, 21/22: 9.7, 22/23: 10.0, 22/38: 6.6, 26/27: 11.1, 29a and 29b/30: 5.8, 29a/29b: not determined, 32/35a: 3.0, 32/35b: 10.3, 35a/35b: 11.6.
9. ROESY correlations for macrocyclic ring portion of 1 [H/H (s: strong, m: medium, w: weak)]: 3/4 (s), 3/5 (m), 3/6 (w), 3/43 (w), 4/6 (s), 4/44 (s), 5/42 (s), 5/43 (m); 6/8 (s), 6/39 (m), 8/10b (s), 8/39 (m), 8/41 (w), 9/10a (s), 9/10b (w), 9/11 (m), 9/42 (s), 10a/11 (m), 10a/41 (w), 10b/11 (w), 10b/12 (m), 10b/39 (w), 10b/41 (w), 11/40 (s), 12/15a (s), 12/17 (m), 12/39 (w), 14/15a (w), 14/15b (m), 14/16b (m), 14/17 (m), 14/40 (s), 15a/16a (w), 15a/15b (m), 15a/17 (w), 15a/18 (m), 15b/16a (m), 15b/16b (m), 16a/17 (m), 16a/18 (w), 16b/17 (m), 16b/18 (s), 16b/39 (w), 17/19 (s), 18/20 (s), 18/39 (w), 19/21 (s), 19/39 (w), 20/22 (s), 20/38 (w), 20/44 (w), 21/22 (w), 21/23 (m), 21/38 (m), 22/26 (w), 22/37 (s), 23/26 (s), 23/27 (w), 23/38 (m), 26/29 (s), 26/36 (w), 26/38 (w), 27/29 (m), 27/37 (s), 29/36 (s), 37/38 (w), 39/44 (m), 41/42 (s), and 42/43 (w).
10. Matsumori N., Kaneno D., Murata M., Nakamura H., Tachibana K. J. Org. Chem. 64:1999;866-876.
11. Clark M., Cramer R.D. III, Van Opdenbosch N. J. Comp. Chem. 10:1989;982-1012.
12. 8 for iejimalide B (1). For 1, 100 conformers were generated. In simulated annealing simulation, each conformation was equilibrated for 5000 fs in a thermal bath at 1000 K, and thereafter successively for 1450 fs, the temperature was deceased until a final structure of 300 K was reached, and each conformation was finally minimized.
13. total, 34.28±0.24 kcal/mol, RMSD, 0.62±0.09 Å; distance RMS violation, 1.080±0.01.
14. 6Na, 615.1793].
15. Hannesian S., Ugolini A., Therein M. J. Org. Chem. 48:1983;4427-4430.
16. 6Na, 615.1793].
17. 6Na, 615.1793].