Absolute Construction of the Whole Mother Skeleton of Hemibrevetoxin-B

Synlett

Volumn 1996, Issue 4, 1996, Pages 363-365

  Ishihara, Jun ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000575713     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5435     Document Type: Article

References (15)

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4. For syntheses of hemibrevetoxin-B (1); a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1993, 115, 3558. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1992, 114, 7935. b) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett., 1995, 36, 5777. For synthetic studies of 1; c) Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett., 1996, 37, 217.
5. For syntheses of hemibrevetoxin-B (1); a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1993, 115, 3558. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1992, 114, 7935. b) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett., 1995, 36, 5777. For synthetic studies of 1; c) Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett., 1996, 37, 217.
6. For syntheses of hemibrevetoxin-B (1); a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1993, 115, 3558. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1992, 114, 7935. b) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett., 1995, 36, 5777. For synthetic studies of 1; c) Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett., 1996, 37, 217.
7. For syntheses of hemibrevetoxin-B (1); a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1993, 115, 3558. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1992, 114, 7935. b) Kadota, I.; Park, J.-Y.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett., 1995, 36, 5777. For synthetic studies of 1; c) Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett., 1996, 37, 217.
8. a) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett., 1989, 1313.
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14. 3), δ4.75 (1H, d, J=7.7 Hz), 4.60 (1H, d, J=7.7 Hz), 4.63 (2H, s), 4.00 (1H, dd, J=7.0 and 10.6 Hz), 4.00-3.98 (1H, m), 3.91-3.85 (1H, m), 3.77 (1H, dd, J=5.1 and 10.6 Hz), 3.68 (1H, ddd, J=4.9 Hz, 9.9 Hz, and 11.7 Hz), 3.58-3.53 (2H, m), 3.36 (3H, s), 3.34 (3H, s), 3.35-3.26 (2H, m), 3.24-3.20 (2H, m), 2.21-2.16 (1H, m), 2.07-1.75 (9H, m), 1.66-1.51 (4H, m), 1.37-1.25 (2H, m), 1.22 (3H, s), 1.10 (3H, s), 0.91 (9H, s), and 0.09 (6H, s).
15. NOE differencial experiments were shown as follows; (Equation Presented)