Synthetic studies on the common C25 long chain acid portion of zooxanthellatoxins from a symbiotic dinoflagellate symbiodinium sp

Tetrahedron Letters

Volumn 37, Issue 18, 1996, Pages 3153-3156

  Nakamura, Hideshi ^a   Fujimaki, Kazuhiro ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DINOPHYCEAE; SYMBIODINIUM;

TOXIN; UNCLASSIFIED DRUG; ZOOXANTHELLATOXIN;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029919011     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00515-1     Document Type: Article

References (19)

1. Faulkner, D., J. Nat. Prod. Rep. 1995, 223-269, and the references cited therein.
2. Shimizu, Y. Chem. Rev. 1993, 93, 1685-1698.
3. Yasumoto, T.; Murata, M., Chem. Rev. 1993, 93, 1897-1909.
4. Nakamura, H.; Asari, T.; Matsuoka, S.; Ohizumi, Y.; Kobayashi, J.; Yamasu, T.; Murai, A. Toxicon, 1993, 31, 371-376.
5. (a) Nakamura, H.; Asari, T.; Fujimaki, K.; Maruyama, K.; Murai, A.; Ohizumi, Y.; Kan, Y. Tetrahedron Lett., 1995, 36, 7255-7258.
6. (b) Nakamura, H.; Asari, T.; Murai, A.; Kan, Y.; Kondo, T.; Yoshida, K.; Ohizumi, Y. J. Am. Chem. Soc., 1995, 117, 550-551.
7. (c) Nakamura, H.; Asari, T.; Murai, A.; Kondo, T.; Yoshida, K.; Ohizumi, Y. J. Org. Chem., 1993, 58, 313-314.
8. (d) Asari, T.; Nakamura, H.; Murai, A.; Kan, Y. Tetrahedron Lett., 1993, 34, 4059-4062.
9. Rho, M. -C.; Nakahata, N.; Nakamura, H.; Murai, A.; Ohizumi, Y. Br. J. Pharmacol. 1995, 115, 433-440.
10. All new compounds gave satisfactory spectral data.
11. Richtmyer, N. K., Methods in Carbohydrate Chemistry, 1962, 1, 107-113.
12. 10 389.1448.
13. 6 274.1417.
14. Kolb, H. C.; VanNieuwenhze, M., S.; Sharpless, K., B. Chem. Rev., 1994, 94, 2483-2547.
15. 3).
16. Dihydroxylation of the cis-olefin alcohol with AD-mix-α was not diastereoselective and gave a mixture of possible diol isomers.
17. Ohtani, I., Kusumi, T., Kashman, Y., and Kakisawa, H., J. Am. Chem. Soc., 1991, 113, 4092-4096.
18. 3) δ 1.37 (3H, s), 1.46 (3H, s), 1.47 (3H, s), 1.53 (1H, m), 1.70 (1H, m), 1.80-2.05 (4H, m), 2.02 (1H, d, J=15 Hz), 2.32 (1H, dd, J=15, 6 Hz), 2.55 (1H, d, J=6 Hz), 3.24 (3H, s), 3.34 (3H, s), 3.42 (1H, dt, J=10, 3 Hz), 3.73 (1H, m), 3.86 (1H, dd, J=10, 6 Hz), 3.98 (1H, dt, J=7, 5 Hz), 4.17 (2H, m), 4.43 (1H, d, J=6 Hz), 5.05 (1H, dd, J=5, 1 Hz).
19. 3) δ 1.25 (3H, s), 1.50-1.72 (2H, m), 1.76-1.96 (3H, m), 2.12 (1H, d, J=15 Hz), 2.07-2.17 (1H, m), 2.23 (1H, dd, J=15, 6 Hz), 3.26 (3H, s), 3.28 (3H, s), 3.98 (1H, t, J=9 Hz), 4.11 (1H, t, J=3 Hz), 4.24 (1H, m), 4.32 (1H, m), 5.03 (1H, d, J=5 Hz), 5.34 (1H, dd, J=4, 3 Hz), 5.54 (1H, m), 5.79 (1H, t, J=3 Hz), 7.23 (2H, t, J=8 Hz), 7.32 (2H, t, J=8 Hz), 7.45 (2H, t, J=8 Hz), 7.48 (1H, t, J=8 Hz), 7.49 (1H, t, J=8 Hz), 7.60 (1H, t, J=8 Hz), 7.82 (2H, d, J=8 Hz), 7.84 (2H, d, J=8 Hz), 8.08 (2H, d, J=8 Hz); CD (2-propanol) 237.5 nm (Δε +5.9) and 224.0 nm (-3.0). 2b from 1: CD (2-propanol) 237.5 nm (+3.3) and 224.0 nm (-2.2).