Thermolysis of taxinine and taxinine H. Allylic rearrangement of the ester moiety in the C-ring

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 8, 1998, Pages 1314-1316

  Suzuki, Hikokazu ^a   Sako, Magoichi ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

(2 ,9 ,10 triacetoxy 8 ,12,15 ,15 tetramethyl 13 oxotricyclo 9.3.1.03,8 pentadeca 4,11 dien 4 yl)methanol; 2 ,9 ,10 triacetoxy 8 ,12,15 ,15 tetramethyl 4 methylene 13 oxotricyclo 9.3.1.03.8 pentadeca 5,11 diene; Allylic rearrangement; Taxinine; Taxinine H; Thermolysis

Indexed keywords

PACLITAXEL DERIVATIVE; TAXININE DERIVATIVE; TAXININE H; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; DEACYLATION; DRUG SYNTHESIS; NONHUMAN; PHOTOLYSIS; THERMAL EXPOSURE;

EID: 0031756307     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1314     Document Type: Article

References (13)

1. Sako M., Suzuki H., Yamamoto N., Hirota K., Maki Y., J. Chem. Soc., Perkin Trans. 1, 1998, 417-422.
2. 3,8]pentadec-11-en-5α-yl) ester.
3. Kingston D. G. I., Molinero A. A., Rimoldi J. M., "Progress in the Chemistry of Organic Natural Products," Vol. 61, ed. by Herz W., Kirby G. W., Moore R. E., Steglich W., Tamm Ch., Springer-Verlag, Wien, 1993, p. 19.
4. Kobayashi J., Hosoyama H., Wang X.-X., Shigemori H., Koiso Y., Iwasaki S., Sasaki T., Naito M., Tsuruo T., Bioorg. Med. Chem. Lett., 7, 393-398 (1997).
5. 3,8]pentadec-11-en-2α-yl) ester.
6. Rohr J., Angew. Chem., 109, 2284-2289 (1997) and references cited therein.
7. Farina V., "The Chemistry and Pharmacology of Taxol and Its Derivatives," (Pharmacochemistry Library, Vol. 22), ed. by Timmerman H., Elsevier, Amsterdam, 1995.
8. 3,8]pentadec-11-en-5α-ol.
9. Altenbach H.-J., "Comprehensive Organic Synthesis," Vol. 6, ed. by Trost B. M., Fleming I., Pergamon Press, Oxford, 1991, pp. 829-867.
10. Morita H., Wei L., Gonda A., Takeya K., Itokawa H., Fukaya H., Shigemori H., Kobayashi J., Tetrahedron, 53, 4621-4626 (1997).
11. Yamamoto Y., Uyeo S., Ueda K., Chem. Pharm. Bull., 12, 386-388 (1964).
12. Kobayashi T., Kurono M., Sato H., Nakanishi K., J. Am. Chem. Soc., 94, 2863-2865 (1972); Kobayashi J., Ogiwara A., Hosoyama H., Shigemori H., Yoshida N., Sasaki T., Li Y., Iwasaki S., Naito M., Tsuruo T., Tetrahedron, 50, 7401-7416 (1994).
13. Kobayashi T., Kurono M., Sato H., Nakanishi K., J. Am. Chem. Soc., 94, 2863-2865 (1972); Kobayashi J., Ogiwara A., Hosoyama H., Shigemori H., Yoshida N., Sasaki T., Li Y., Iwasaki S., Naito M., Tsuruo T., Tetrahedron, 50, 7401-7416 (1994).