Asymmetric synthesis of aerothionin, a marine dimeric spiroisoxazoline natural product, employing optically active spiroisoxazoline derivative

Tetrahedron Letters

Volumn 47, Issue 5, 2006, Pages 727-731

  Ogamino, Takahisa ^a   Obata, Rika ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Aerothionin; Bromotyrosine; Diastereomeric separation; Spiroisoxazoline

Indexed keywords

AEROTHIONIN; ISOXAZOLINE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; RACEMIZATION;

EID: 29544443056     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.097     Document Type: Article

References (36)

1. D.J. Faulkner Nat. Prod. Rep. 19 2002 1 48 and references cited therein
2. E. Fattorusso, L. Minale, G. Sodano, K. Moody, and R.H. Thomson J. Chem. Soc., Chem. Commun. 1970 752 753
3. K. Moody, R.H. Thomson, E. Fattorusso, L. Minale, and G. Sodano J. Chem. Soc., Perkin Trans. 1 1972 18 24
4. J.A. McMillan, I.C. Paul, Y.M. Goo, K.L. Rinehart Jr., W.C. Krueger, and L.M. Pschigoda Tetrahedron Lett. 22 1981 39 42
5. B.M. Saeki, A.C. Granato, R.G.S. Berlinck, A. Magalháes, A.B. Schfer, A.G. Ferreira, U.S. Pinheiro, and E. Hajdu J. Nat. Prod. 65 2002 796 799
6. Y. Gopichand, and F.J. Schmits Tetrahedron Lett. 41 1979 3921 3924
7. R.D. Encarnación, E. Sandoval, J. Malmstrøm, and C. Christophersen J. Nat. Prod. 63 2000 874 875
8. M.R. Kernan, R.C. Canbie, and P.R. Bergquist J. Nat. Prod. 53 1990 615 622
9. A.L. Acosta, and A.D. Rodríguez J. Nat. Prod. 55 1992 1007 1012
10. S.P. Grunasekera, and S.S. Cross J. Nat. Prod. 55 1992 509 512
11. G.M. König, and A.D. Wright Heterocycles 36 1993 1351 1358
12. I. Mancini, G. Guella, P. Laboute, C. Debitus, and F. Pietra J. Chem. Soc., Perkin Trans. 1 1993 3121 3125
13. R.S. Compagnone, R. Avila, A.I. Suárez, O.V. Abrams, H.R. Rangel, F. Arvelo, I.C. Piña, and E. Merentes J. Nat. Prod. 62 1999 1443 1444
14. K.A. El Sayed, P. Bartyzel, X. Shen, T.L. Perry, J.K. Zjawiony, and M.T. Hamann Tetrahedron 56 2000 949 953
15. P. Ciminiello, C.D. Aversano, E. Fattorusso, and S. Magno Eur. J. Org. Chem. 2001 55 60
16. Y. Okamoto, M. Ojika, S. Kato, and Y. Sakagami Tetrahedron 56 2000 5813 5818
17. H.H. Wasserman, and J. Wahng J. Org. Chem. 63 1998 5581 5586
18. K. Goldenstein, T. Fendert, P. Proksch, and E. Winterfeldt Tetrahedron 56 2000 4173 4185
19. T.R. Boehlow, J. Jonathan Harburn, and C.D. Spilling J. Org. Chem. 66 2001 3111 3118
20. S. Nishiyama, and S. Yamamura Tetrahedron Lett. 24 1983 3351 3352
21. S. Nishiyama, and S. Yamamura Bull. Chem. Soc. Jpn. 58 1985 3453 3456
22. M. Murakata, K. Yamada, and O. Hoshino J. Chem. Soc., Chem. Commun. 1994 443 444
23. M. Murakata, K. Yamada, and O. Hoshino Tetrahedron 52 1996 14713 14722
24. M. Murakata, M. Tamura, and O. Hoshino J. Org. Chem. 62 1997 4428 4433
25. M. Murakata, K. Yamada, and O. Hoshino Heterocycles 47 1998 921 931
26. T. Ogamino, Y. Ishikawa, and S. Nishiyama Heterocycles 61 2003 73 79
27. T. Ogamino, and S. Nishiyama Tetrahedron 59 2003 9419 9423
28. +, 574.9790.
29. Optical purity analysis of 10 by chiral HPLC showed large difference in the retention times (10R: 18 min, 10S: 26 min), although the enantiomers of 8 were not separated.
30. K. Goldenstein, T. Fendert, P. Proksch, and E. Winterfeldt Tetrahedron 56 2000 4173 4185
31. T. Ogamino, and S. Nishiyama Tetrahedron Lett. 46 2005 1083 1086
32. (b) Ogamino, T.; Obata, R.; Tomoda, H.; Nishiyama, S. Bull. Chem. Soc. Jpn., in press.
33. 5 In addition, comparison with the wave length of the CD spectra reported indicated the absolute structure of calafianin (5) might be as depicted in Figure 1.
34. D.B. Cosulich, and F.M. Lovell J. Chem. Soc., Chem. Commun. 1971 397 398
35. W. Fulmor, G.E. Van Lear, G.O. Morton, and R.D. Mills Tetrahedron Lett. 11 1970 4551 4552
36. 2c.