Structures of fukinone epoxides. Configuration, conformation, and CD spectra

Heterocycles

Volumn 82, Issue 2, 2010, Pages 1719-1726

  Saito, Yoshinori ^a   Tori, Motoo ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952742106     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-S(E)118     Document Type: Article

References (19)

1. M. Tori, K. Nakashima, M. Toyota, and Y. Asakawa, Tetrahedron Lett., 1993, 34, 3751;
2. M. Tori, H. Arbiyanti, Z. Taira, and Y. Asakawa, Tetrahedron Lett., 1992, 33, 4011;
3. Y. Asakawa, X. Lin, M. Tori, and K. Kondo, Phytochemistry, 1990, 29, 2597;
4. H. M. Chen, M. S. Cai, and Z. J. Jia, Phytochemistry, 1997, 45, 1441;
5. S. Ito, M. Sunagawa, M. Kodama, and H. Honma, J. Chem. Soc., Chem. Commun, 1971, 91.
6. The structures of new compounds (a pair of 6-acetoxy-7,11- epoxyeremophilan-8-one) from Ligularia subspicata and L. lamarum collected in China and the diversity in these species will be reported in due course.
7. K. Hayashi, H. Nakamura, and H. Mitsuhashi, Chem. Pharm. Bull., 1973, 21, 2806.
8. In ref. 3, epoxide A had mp 64-66°C, [α]d +24 (c 0.5 MeOH), (+)-Cotton effect, NMR (CCl4) δ 0.98 (3H, d, J = 6 Hz), 1.13 (6H, s), 1.32 (3H, s); epoxide B had mp 83-83.5 °C, [α]d +21 (c 0.51, MeOH), (-)-Cotton effect, NMR (CCl4) 5 0.90 (3H, d, J = 6 Hz), 0.96 (3H, s), 1.12 (3H, s), 1.35 (3H, s).
9. A. Horinaka and K. Naya, Bull. Chem. Soc. Jpn., 1979, 52, 1964.
10. In ref. 5, epoxide 2 had mp 66-67°C; epoxide 3 had mp 83-84 °C.
11. W. Reusch and C. K. Johnson, J. Org. Chem, 1963, 28, 2557;
12. W. Reusch and P. Mattison, Tetrahedron, 1968, 24, 4933.
13. C. Djerassi, W. Klyne, T. Norin, G. Ohloff, and E. Klein, Tetrahedron, 1965, 21, 163;
14. G. Snatzke, Tetrahedron, 1965, 21, 421;
15. H. Wynberg and B. Marsman, J. Org. Chem., 1980, 45, 158.
16. X-Ray crystallographic analysis of compound 5: All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). Mo Kα radiation, k = 0.71073 Å, Data collection: DIP Image plate, Program(s) used to refine structure: SHELXL-97 (Sheldrick, 1997); refinement on F2, full matrix least squares refinement. Crystal data: orthorhombic, p212121, a = 6.4711(8) Å, b = 10.6378(12) Å, c = 34.182(4) Å, α = 90°, β = 90°, γ = 90°, V = 2353.0(5) Å3, R = 0.0359. Crystallographic data for compound 5 have been deposited at the Cambridge Crystallographic Data Center as supplementary publication number CCDC 790131. Copies of the data can be obtained, free of charge, via www.ccdc.cam.ac.uk/data-request/cif, or by mailing to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: data-request@ccdc.cam.ac.uk).
17. X-Ray crystallographic analysis of compound 8: All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). Mo Kα radiation, k = 0.71073 Å, Data collection: DIP Image plate, Program(s) used to refine structure: SHELXL-97 (Sheldrick, 1997); refinement on F2, full matrix least squares refinement. Crystal data: monoclinic, p21, a = 11.603(13) Å, b = 7.146(8) Å, c = 14.644(16) Å, α = 90°, β = 107.887(14)°, γ = 90°, V = 1155(2) Å3, R = 0.0784. Crystallographic data for compound 8 have been deposited at the Cambridge Crystallographic Data Center as supplementary publication number CCDC 790130. Copies of the data can be obtained, free of charge, via www.ccdc.cam.ac.uk/data-request/cif, or by mailing to the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: data-request@ccdc.cam.ac.uk).
18. M. Tori, H. Nakamizo, K. Mihara, M. Sato, Y. Okamoto, K. Nakashima, M. Tanaka, Y. Saito, X. Gong, Y. Shen, R. Hanai, and C. Kuroda, Phytochemistry, 2008, 69, 1158;
19. M. Tori, A. Watanabe, S. Matsuo, Y. Okamoto, K. Tachikawa, S. Takaoka, X. Gong, C. Kuroda, and R. Hanai, Tetrahedron, 2008, 64, 4486.