Stereoselective epoxidation of 4(20)-exomethylene in taxinine derivatives and assignment of the epoxide orientation by NMR

Tetrahedron

Volumn 54, Issue 11, 1998, Pages 2521-2528

  Hosoyama, Hirokazu ^a   Shigemori, Hideyuki ^a   In, Yasuko ^b   Ishida, Toshimasa ^b   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1BETA HYDROXYBACCATIN; TAXININE; TAXOID; UNCLASSIFIED DRUG;

ARTICLE; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032510261     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00018-0     Document Type: Article

References (16)

1. 1. Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. Progress in the Chemistry of Organic Natural Products 1993, 61, 1-206 and references cited therein.
2. 2. Appendino, G. Nat. Prod. Rep., 1995, 349-360.
3. 3. Appendino, G.; Cravotto, G, Enriú, R.; Gariboldi, P.; Barboni, L, Torregiani, E.; Gabetta, B.; Zini, G.; Bombardelli, E. J. Nat. Prod. 1994, 57, 607-613.
4. 4. Della Casa De Marcano, D. P.; Halsall, T. G. J. Chem. Soc. D (Chem. Commun)., 1970, 1381-1382.
5. 5. Kobayashi, J.; Ogiwara, A.; Hosoyama, H; Shigemori, H.; Yoshida, N.; Sasaki, T.; Li, Y.; Iwasaki, S.; Naito, M.; Tsuruo, T. Tetrahedron 1994, 50, 7401-7416.
6. 6. a) Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
7. b) Ferrer, M.; Gilbert, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron Lett. 1996, 37, 3585-3586.
8. d) (24); a) Barboni, L.; Gariboldi, P.; Torregiani, E.; Appendino, G.; Gabetta, B.; Zini, G.; Bombardelli, E. Phytochemistry, 1993, 33, 145-150.
9. b) Zamir, L. O.; Nadea, M. E.; Bélair, S.; Sauriol, F.; Mamer, O.; Jacqmain, E.; Jean, F. I.; Garneau, F. X. Tetrahedron Lett., 1992, 33, 5173-5176: corrigendum, Tetrahedron Lett., 1992, 33, 6548.
10. b) Zamir, L. O.; Nadea, M. E.; Bélair, S.; Sauriol, F.; Mamer, O.; Jacqmain, E.; Jean, F. I.; Garneau, F. X. Tetrahedron Lett., 1992, 33, 5173-5176: corrigendum, Tetrahedron Lett., 1992, 33, 6548.
11. c) Ettouati, L.; Ahond, A.; Convert, O.; Poupat, C.; Potier, P. Bull. Soc. Chim. Fr., 1989, 687-694.
12. d) Hosoyama, H.; Inubushi, A.; Katsui, T.; Shigemori, H.; Kobayashi, J. Tetrahedron, 1996, 52, 13145-13150.
13. 8. Adam, W.; Chan, Y. -Y.; Cremer, D.; Gauss, J.; Scheutzow, D.; Schindler, M. J. Org. Chem. 1987, 52, 2800-2803.
14. 9. Kobayashi, J.; Inubushi, A.; Hosoyama, H.; Yoshida, N.; Sasaki, T.; Shigemori, H. Tetrahedron 1995, 51, 5971-5978.
15. 10. Sheldrick, G. M. SHELXL93. Program for the Refinement of Crystal Structure, University of Göttingen, Göttingen, 1993.
16. 11. Lists of structure factors, anisotropic distancement parameters, H-atom coordinates and complete geometry have been deposited with the IUCr (Reference: AS1088).