Isolation of dephosphonocalyculin A from the marine sponge, discodermia calyx

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3763-3764

  Matsunaga, Shigeki ^a   Wakimoto, Toshiyuki ^a   Fusetani, Nobuhiro ^a   Suganuma, Masami ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b SAITAMA CANCER CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALYCULIN A; ENZYME INHIBITOR; PHOSPHOPROTEIN PHOSPHATASE 1;

ARTICLE; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; LEUKEMIA P 388; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPONGE; STEREOCHEMISTRY;

EID: 0030904582     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00748-X     Document Type: Article

References (12)

1. Bioactive marine metabolites. 80. Part 79: Fukuzawa, S.; Matsunaga, S.; Fusetani, N., submitted for publication.
2. Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K.; Fujita, S.; Furuya, T. J. Am. Chem. Soc. 1986, 108, 2780-2781.
3. Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1991, 32, 5605-5606, and references cited therein.
4. Total synthesis of calyculin A: Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.; Tanimoto, N.; Gerritz, S. W.; Sawabe, A.; Noda, T.; Filla, S. A.; Masamune, S. Angew. Chem. 1994, 106, 674-677.
5. Total synthesis of calyculin A: Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434-9453.; Tanimoto, N.; Gerritz, S. W.; Sawabe, A.; Noda, T.; Filla, S. A.; Masamune, S. Angew. Chem. 1994, 106, 674-677.
6. Suganuma, M.; Fujiki, H.; Furuya-Suguri, H.; Yoshizawa, S.; Yasumoto, S.; Kato, Y.; Fusetani, N.; Sugimura, T. Cancer Res. 1990, 50, 3521-3525.
7. Ishihara, H.; Martin, B. L.; Brautigan, D. L.; Karaki, H.; Ozaki, H.; Kato, Y.; Fusetani, N.; Watabe, S.; Hashimoto, K.; Uemura, D.; Hartshorne, D. J. Biochem. Biophys. Res. Commun. 1989, 159, 871-877.
8. Matsunaga, S.; Wakimoto, T.; Fusetani, N. J. Org. Chem., in press.
9. 3OD); δ 95.5 (C-2), 159.0 (C-3), 129.2 (C-4), 135.1 (C-5), 125.7 (C-6), 146.0 (C-7), 137.5 (C-8), 132.4 (C-9), 37.5 (C-10), 78.9 (C-11), 44.2 (C-12), 70.9 (C-13), 30.0 (C-14), 81.2 (C-15), 87.1 (C-16), 80.5 (C-17), 48.5 (C-18), 109.5 (C-19), 34.1 (C-20), 71.8 (C-21), 38.5 (C-22), 68.2 (C-23), 37.5 (C-24), 130.0 (C-25), 122.5 (C-26), 139.5 (C-27), 136.5 (C-28), 169.7 (C-29), 32.9 (C-30), 35.4 (C-31), 38.0 (C-32), 175.0 (C-33), 76.1 (C-34), 71.2 (C-35), 65.0 (C-36), 70.1 (C-37), 58.4 (C-38), 42.5 (C-39,40) 18.6 (C-41), 11.6 (C-42), 22.0 (C-43), 16.6 (C-44), 60.1 (C-45), 11.4 (C-46), 18.4 (C-47), 14.2 (C-48), 14.6 (C-49), 19.2 (C-50).
10. + m/z 1049]. Subsequently, 3 was heated with a mixture of pyridine/dioxane (1:1, 0.3 mL) at 120 °C for 4 days. The reaction mixture was separated by HPLC on ODS to afforded 4 (1 mg).
11. + m/z 969].
12. Bagu, J. R.; Sykes, B. D.; Craig, M. M.; Holmes, C. F. B. J. Biol. Chem. 1997, 272, 5087-5097, and references cited therein.