Synthetic study of pinnatoxin A: Stereoselective synthesis of the BCD-ring unit, a novel 6,5,6-bis-spiroketal system

Synlett

Volumn , Issue 3, 1998, Pages 298-300

  Noda, Takeshi ^a,b   Ishiwata, Akihiro ^a   Uemura, Satoshi ^a   Sakamoto, Satoshi ^a   Hirama, Masahiro ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002504638     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1648     Document Type: Article

References (23)

1. Zheng, S. Z.; Huang, F. L.; Chen, S. C.; Tan, X. F.; Zuo, J. B.; Peng, J. and Xie, R. W. Zhongguo HaiyangYaowu (Chinese J. of Marine Drugs). 1990, 33, 33.
2. Ueraura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.; Chen, H. J. Am. Chem. Soc. 1995, 117, 1155.
3. Chou, T.; Kamo, O. and Uemura, D. Tetrahedron Lett. 1996, 37, 4023.
4. Synthesis of the spiroketal unit has been reported very recently: Sugimoto, T.; Ishihara, J. and Murai, A. Tetrahedron Lett. 1997, 38, 7379.
5. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983;
6. Juaristi, E.; Cuevas, G. The Anomeric Effect; CRC Press: Boca Raton, 1995.
7. For reviews of spiroketal, see: Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
8. Corey, E. J.; Achiwa, K.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 4318;
9. McMurry, J. E.; Erion, M. D. J. Am. Chem. Soc. 1985, 107, 2712.
10. Masamune, S.; Ma, P.; Okumoto, H.; Ellingboe, J. W.; Ito, Y. J. Org. Chem. 1984, 49, 2834.
11. Clark, J. H. and Miller, J. M. J. Chem. Soc., Perkin Trans. 1 1977, 1743.
12. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765;
13. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719.
14. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D. and Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
15. Brimble, M. A.; Rush, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 497;
16. McGarvey, G. J.; Stepanian, M. W. Tetrahedron Lett. 1996, 37, 5461;
17. McGarvey, G. J.; Stepanian, M. W.; Bressette, A. R.; Ellena, J. F. Tetrahedron Lett. 1996, 37, 5465.
18. 3, 600MHz) 7.68-7.63 (m, 4H, Ph), 7.44-7.36 (m, 6H, Ph), 4.04 (dddd, 1H, J=11.2, 5.8, 3.8, 2.3Hz, C23-H), 3.98 (dd, 1H, J=11.2, 5.8Hz, C24-Ha), 3.88 (dtd, 1H, J=11.8, 6.5, 2.5Hz, C12-H), 3.86 (dd, 1H, J=11.2, 3.8Hz, C24-Hb), 3.79 (ddd, 1H, J=10.3, 7.8, 7.0Hz, C10-Ha), 3.71 (ddd, 1H, J=10.3, 8.0, 5.5Hz, C10-Hb), 2.24 (s, 1H, C15-OH), 2.16 (m, 1H, C17-Ha), 2.12 (m, 1H, C18-Ha), 2.00 (s, 3H, Ac), 1.87 (dddd, 1H, J=14.0, 8.0, 7.0, 6.5Hz, C11-Ha), 1.83 (m, 1H, C21-Heq), 1.82 (m, 1H, C18-Hb), 1.80 (m, 1H, C17-Hb), 1.78 (m, 1H, C14-Hax), 1.73 (m, 1H, C21-Hax), 1.72 (m, 1H, C20-Heq), 1.70 (m, 7H, C11-Hb), 1.67 (m, 1H, C14-Heq), 1.62 (m, 1H, C20-Hax), 1.57 (m, 1H, C13-Heq), 1.52 (m, 1H, C22-Heq), 1.41 (tdd, 1H, J=13.5, 12.0, 4.2Hz, C13-Hax), 1.28 (tdd, 1H, J=13.0, 12.0, 4.2Hz, C22-Hax), 1.22 (s, 3H, C15-Me), 1.05 (s, 9H, tBu).
19. 3, 600MHz) 7.68-7.63 (m, 4H, Ph), 7.44-7.35 (m, 6H, Ph), 4.17 (dd, 1H, J=11.3, 7.2Hz, C24-Ha), 4.05 (dd, 1H, J=11.3, 4.0Hz, C24-Hb), 4.03 (m, 1H, C12-H), 3.78 (dddd, 1H, J=11.2, 7.2, 4.0, 3.5Hz, C23-H), 3.79 (ddd, 1H, J=10.3, 7.2, 6.0Hz, C10-Ha), 3.71 (dt, 1H, J=10.3, 6.0Hz, C10-Hb), 2.93 (brs, 1H, C15-OH), 2.29 (td, 1H, J=12.2, 7.6Hz, C17-Ha), 2.12 (dd, 1H, J=12.6, 7.6Hz, C18-Ha), 2.07 (s, 3H, Ac), 1.89 (td, 1H, J=13.5,4.8Hz, C14-Hax), 1.83 (dtt, 1H, J=13.2, 4.7, 4.3Hz, C21-Heq), 1.74 (td, 1H, J=12.6, 8.0Hz, C18-Hb), 1.70 (m, 1H, C20-Heq), 1.68 (m, 1H, C11-Ha), 1.67 (m, 1H, C20-Hax), 1.64 (dd, 1H, J=12.2, 8.0Hz, C17-Hb), 1.63 (m, 1H, C14-Heq), 1.60 (m, 1H, C11-Hb), 1.56 (m, 1H, C22-Heq), 1.54 (m, 1H, C13-Heq), 1.48 (tdt, 1H, J=13.2, 12.0, 4.0Hz, C21-Hax), 1.41 (tdd, 1H, J=13.5, 12.0, 4.2Hz, C13-Hax), 1.30 (dddd, 1H, J=13.5, 11.5, 10.0, 4.0Hz, C22-Hax), 1.22 (s, 3H, C15-Me), 1.04 (s, 9H, tBu).
20. The structures of the minor isomers were not determined.
21. -3, R = 0.037.
22. Gao, Y.; Zepp, C. M. Tetrahedron Lett. 1991, 32, 3155;
23. Mori, K.; Takigawa, T.; Matsuo, T. Tetrahedron 1979, 35, 933.