Asymmetric synthesis of a C1-C19 fragment of ulapualide A

Tetrahedron Letters

Volumn 43, Issue 39, 2002, Pages 7043-7046

  Celatka, Cassandra A ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

Marine metabolites; Tris oxazole; Ulapualide A

Indexed keywords

ANTIFUNGAL AGENT; ULAPUALIDE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CROTYLATION; DRUG OXIDATION; DRUG SYNTHESIS; HYDROLYSIS; KISHI NOZAKI COUPLING; STEREOCHEMISTRY;

EID: 0037163254     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01553-8     Document Type: Article

References (29)

1. Roesener J.A., Scheuer P.J. J. Am. Chem. Soc. 108:1986;846-847.
2. Fusetani N., Yasumuro K., Matsunaga S., Hashimoto K. Tetrahedron Lett. 30:1989;2809-2812.
3. Rashid M.A., Gustafson K.R., Cardellina J.H. II, Boyd M.R. J. Nat. Prod. 58:1995;1120-1125.
4. Matsunaga S., Sugawara T., Fusetani N. J. Nat. Prod. 61:1998;1164-1167.
5. Matsunaga S., Fusetani N., Hashimoto K. J. Am. Chem. Soc. 108:1986;847-849.
6. Matsunaga S., Fusetani N., Hashimoto K., Koseki K., Noma M., Noguchi H., Sankawa U. J. Org. Chem. 54:1989;1360-1363.
7. Kernan M.R., Molinski T.F., Faulkner J.D. J. Org. Chem. 53:1988;5014-5020.
8. Kobayashi J., Murata O., Shigemori H. J. Nat. Prod. 56:1993;787-791.
9. Kobayashi J., Tsuda M., Fuse H., Sasaki T., Mikami Y. J. Nat. Prod. 60:1997;150-154.
10. The numbering system employed for ulapualide is based on the same numbering system used for the mycalolides.
11. Matsunaga S., Liu P., Celatka C.A., Panek J.S., Fusetani N. J. Am. Chem. Soc. 121:1999;5605-5606.
12. Fusetani, N.; Matsunaga, S. 2000, personal communication.
13. . The C9 stereocenter is tentatively based on molecular mechanics studies predicting the lowest energy conformation of a metal-chelate complex of ulapualide A: Maddock J., Pattenden G., Wight P.G. J. Comput. Aided Mol. Des. 7:1993;573-586.
14. . Synthesis of a diastereomer of ulapualide A has been reported: Chattopadhyay S.K., Pattenden G. Tetrahedron Lett. 39:1998;6095-6098.
15. Chattopadhyay S.K., Pattenden F. J. Chem. Soc., Perkin Trans. 1. 2000;2429-2454.
16. Panek J.S., Liu P. J. Am. Chem. Soc. 122:2000;11090-11097.
17. Tokunaga M., Larrow J.F., Kakiuchi F., Jacobsen E.N. Science. 277:1997;936-938.
18. . For review, see: Masse C.M., Panek J.S. Chem. Rev. 95:1995;1293-1316.
19. . Racemic epoxide 4 was prepared by epoxidation of t-butyl vinylacetate with m-CPBA, which was in turn prepared according to the described procedure: Ozeki T., Kusaka M. Bull. Chem. Soc. Jpn. 39:1966;1995-1998.
20. The kinetic resolution yield is expressed as a percentage of the theoretical maximum yield of 50%; the ee was determined by HPLC analysis of the phenylthio derivative of 5 with a Chiracel OD column.
21. Takai K., Nitta K., Utimoto K.I. J. Am. Chem. Soc. 108:1986;7408-7410.
22. Schaus J.V., Jain N., Panek J.S. Tetrahedron. 66:2001;2747-2756.
23. Panek J.S., Beresis R.T. J. Org. Chem. 61:1996;6494-6495.
24. Liu P., Celatka C.A., Panek J.S. Tetrahedron Lett. 38:1997;5449-5452.
25. Wipf P., Lim S. J. Am. Chem. Soc. 117:1995;558-559.
26. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4155-4156.
27. Jin H., Uenishi J., Christ W.J., Kishi Y. J. Am. Chem. Soc. 108:1986;5644-5646.
28. Takai K., Tagashira M., Kuroda T., Oshima K., Utimoto K., Nozaki H. J. Am. Chem. Soc. 108:1986;6048-6050.
29. Mori A., Fujita A., Kajiro H., Nishihara Y., Hiyama T. Tetrahedron. 55:1999;4573-4582.