Stereoselective synthesis of the C-and CD-ring systems of hemibrevetoxin B

Tetrahedron Letters

Volumn 37, Issue 2, 1996, Pages 217-220

  Nakata, Tadashi ^a   Nomura, Sumihiro ^a   Matsukura, Hiroko ^a   Morimoto, Masamichi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HEMIBREVETOXIN B; NEUROTOXIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030053378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02132-9     Document Type: Article

References (18)

1. Visiting Scientist from Tanabe Seiyaku Co., Ltd.
2. Krishna, A. V.; Shimizu, Y.J. Am. Chem. Soc. 1989, 111, 6476.
3. Total synthesis: (a) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y. J. Am. Chem. Soc. 1992, 114, 7935.
4. (b) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc., 1993, 115, 3558.
5. (c) Kadota, I.; Jung-Youl, P.; Koumura, N.; Pollaud, G.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5777. Other synthetic studies:
6. (d) Feng, F.; Murai, A. Chemistry Lett. 1992, 1587.
7. (e) Feng, F.; Murai, A. Chemistry Lett. 1995, 23.
8. Nakata, T.; Nomura, S., Matsukura, H. the preceding paper.
9. 3, MeOH, 0°C ∼ rt (84%); (3) DHP, TsOH, ether, 0°C ∼ it (92%); (4) DIBAH, toluene, -65°C (83%).
10. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5976.
11. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
12. Kotsuki, H.; Kadota, I.; Ochi, M. Tetrahedron Lett. 1989, 30, 1281, 3999.
13. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791.
14. The yield was not yet optimized.
15. 3) δ 1.19 (s, 3H), 2.06 (s, 3H), 3.30 (td, J=6.7, 3.6 Hz, 1H), 3.40 (ddd, J=9.7, 7.1, 2.7 Hz, 1H), 3.57 (dd, J=8.8, 2.9 Hz, 1H), 4.11 (dd, J=11.5, 9.0 Hz, 1H), 4.28 (dd, J=11.5, 2.7 Hz, 1H), 4.39 (d, J=11.2 Hz, 1H), 4.59 (d, J=11.7 Hz, 1H), 4.96 (d, J=10.2 Hz, 1H), 5.03 (dd, J=17.1, 1.9 Hz, 1H), 5.84 (ddt, J=17.1, 10.3, 6.3 Hz, 1H).
16. 3) δ 1.19 (s, 3H), 1.28 (t, J=7.0 Hz, 3H), 2.07 (s, 3H), 2.15 (d, J=1.0 Hz, 3H), 3.23-3.39 (m, 2H), 3.56 (dd, J=8.9, 2.3 Hz, 1H), 4.08 (dd, J=11.6, 8.9 Hz, 1H), 4.14 (q, J=7.2 Hz, 2H), 4.30 (dd, J=11.6, 2.6 Hz, 1H), 4.38 (d, J=11.6 Hz, 1H), 4.60 (J=11.6 Hz, 1H), 5.66 (d like, J=8.9 Hz, 1H).
17. 2), 64.6 (COC=O), 74.1 (COH), 74.8 (COH), 85.4 (CO), 87.3 (CO), 88.0 (CO), 88.7 (CO), 114.9 (C=C-C), 138.7 (C=C-C), 171.0 (OC=O).
18. Ohki, M.; Mori, K.; Matsui, M. Agr. Biol. Chem. 1974, 38, 175.