Total synthesis of ulapualide A, a novel tris-oxazole containing macrolide from the marine nudibranch Hexabranchus sanguineus

Tetrahedron Letters

Volumn 39, Issue 33, 1998, Pages 6095-6098

  Chattopadhyay, Shital K ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; OXAZOLE DERIVATIVE; ULAPUALIDE A; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHELATION; DRUG ISOLATION; DRUG SYNTHESIS; SPONGE (PORIFERA);

HEXABRANCHUS SANGUINEUS; PORIFERA;

EID: 0032514435     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01257-X     Document Type: Article

References (15)

1. 1. Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc., 1986, 108, 846.
2. 2. a) Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem., 1989, 54, 1360.
3. b) Kernan, M. R.; Molinski, T. F.; Faulkner, D. J. J. Org. Chem., 1988, 53, 5014.
4. 3. Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M. J. Am. Chem. Soc., 1986, 108, 847.
5. 4. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett., 1989, 30, 2809.
6. 5. Maddock, J.; Pattenden, G.; Wight, P. G. J. Computer-Aided Molecular Design, 1993, 7, 573.
7. 6. Ishibashi, M.; Moore, R. E.; Patterson, G. M. L.; Xu, C.; Clardy, J. J. Org. Chem., 1986, 51, 5300. For a synthesis of scytophycin see Paterson, I.; Watson, C.; Yeung, K-S.; Wallace, P. A.; Ward, R. A. J. Org. Chem., 1997, 62, 452.
8. 6. Ishibashi, M.; Moore, R. E.; Patterson, G. M. L.; Xu, C.; Clardy, J. J. Org. Chem., 1986, 51, 5300. For a synthesis of scytophycin see Paterson, I.; Watson, C.; Yeung, K-S.; Wallace, P. A.; Ward, R. A. J. Org. Chem., 1997, 62, 452.
9. 7. For a synthesis of the related metabolite aplyronine see Yamada, K.; Ojika, M.; Ishigaki, T.; Yoshida, Y.; Ekimoto, H.; Arakawa, M. J. Am. Chem. Soc., 1993, 115, 11020 and Kigoshi, H.; Ojika, M.; Ishigaki, T.; Suenaga, K.; Mutuo, T.; ibid, 1994, 116, 7443.
10. 7. For a synthesis of the related metabolite aplyronine see Yamada, K.; Ojika, M.; Ishigaki, T.; Yoshida, Y.; Ekimoto, H.; Arakawa, M. J. Am. Chem. Soc., 1993, 115, 11020 and Kigoshi, H.; Ojika, M.; Ishigaki, T.; Suenaga, K.; Mutuo, T.; ibid, 1994, 116, 7443.
11. 8. See Chattopadhyay, S. K.; Pattenden, G. Synlett, 1997, 1345 and extensive references and bibliography contained therein.
12. 9. The carbon skeleton of ulapualide A is numbered as shown in reference 1, reporting its isolation.
13. 10. All new compounds showed satisfactory n.m.r spectroscopic and mass spectrometry data. The C9-methyl carbon absorbed at 6 19.3 p.p.m. in the c.m.r. spectrum of the major (α-methyl ?) diastereoisomer of 8, compared to δ 19.1 p.p.m in natural (C9 α-methyl ?) ulapualide A, and δ 20.0 p.p.m in the minor (β-methyl ?) diastereoisomer of 8. The relevant c.m.r data for synthetic 1 (with corresponding data reported for naturally derived ulapualide in parentheses) were: δ 9.1, C52-Me (9.1); 13.4, C49-Me (13.4); 14.2, C50-Me (15.5); 18.9, C54-Me (18.9); 19.2, C46-Me (19.5); 20.9, OCOMe (20.9); 28.1, C-9 (27.7); 34.0, C29 (34.5); 37.3, C40 (37.2); 39.9, C34 (39.8); 40.4, C38 (40.3); 57.6, C28-OMe (57.6); 57.8, C33-OMe (58.1); 68.7, C3 (68.4); 72.9, C30 (73.0); 80.0, C28 (80); 81.1, C33 (81.8)p.p.m.
14. 11. For earlier work see: Kiefel, M. J.; Maddock, J.; Pattenden, G. Tetrahedron Lett, 1992, 33, 3227. For alternative methods for the synthesis of terminal N-methyl-N-alkenylformamides see: Paterson, I.; Cowden, C.; Watson, C. Synlett, 1996, 209 and references therein.
15. 11. For earlier work see: Kiefel, M. J.; Maddock, J.; Pattenden, G. Tetrahedron Lett, 1992, 33, 3227. For alternative methods for the synthesis of terminal N-methyl-N-alkenylformamides see: Paterson, I.; Cowden, C.; Watson, C. Synlett, 1996, 209 and references therein.