A new route for the construction of the AB-ring core of Taxol

Tetrahedron Letters

Volumn 44, Issue 7, 2003, Pages 1401-1403

  Shimada, Yumi ^a   Nakamura, Makoto ^b   Suzuka, Toshimasa ^a   Matsui, Junji ^a   Tatsumi, Ryo ^a   Tsutsumi, Ken ^a   Morimoto, Tsumoru ^a   Kurosawa, Hideo ^b   Kakiuchi, Kiyomi ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PACLITAXEL;

ARTICLE; CATALYSIS; DRUG STRUCTURE; OXIDATION;

LATEOLABRAX JAPONICUS;

EID: 0037429098     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02868-X     Document Type: Article

References (21)

1. Nicolaou K.C., Dai W.-M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15.
2. Kingston D.G.I. Chem. Commun. 2001;867.
3. For isolation and structural analysis, see: (a) Wani, M. C.; Wall, M, E.; Coggon, P.; Mcphail, A. T. J. Am. Chem. Soc. 1971, 93, 2325.
4. For total synthesis, see: (b) Holton, R. A.; Kim, H.-B.; Somoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C. L.; Vu, P.; Tang, S. H.; Zhang, P. S.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599 and preceding paper;
5. (c) Nicolaou, K. C.; Ueno, H.; Liu, J.-J.; Nanternet, P. G.; Yang, Z.; Rebaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653 and preceding papers;
6. (d) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Cobrun, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843 and preceding paper;
7. (e) Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss, N. E.; Lee, D. S.; Marquess, D. G.; MacGran, P. L.; Meng, W.; Natchus, M. G.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E. J. Am. Chem. Soc. 1997, 119, 2757 and preceding paper;
8. (f) Mukaiyama, T.; Shiina, I.; Iwadera, H.; Saitoh, M.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Tani, Y.; Hasegawa, M.; Yamada, K.; Saitoh, K. Chem.-Eur. J. 1999, 5, 121 and preceding papers;
9. (g) Kusama, H.; Hara, R.; Kawahara, S.; Nishimori, T.; Kashima, H.; Nakamura, N.; Morihira, K.; Kuwajima, I. J. Am. Chem. Soc. 2000, 122, 3811 and preceding papers.
10. For papers of synthetic study of bicyclo[5.3.1]undecanes, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881 and references cited therein;
11. (b) Trost, B. M.; Fray, M. J. Tetrahedron Lett. 1984, 25, 4605.
12. Kakiuchi K., Fukunaga K., Matuo F., Ohnishi Y., Tobe Y. J. Org. Chem. 56:1991;6742.
13. Kakiuchi K., Nakamura I., Matuo F., Nakata M., Ogura M., Tobe Y., Kuroswa H. J. Org. Chem. 60:1995;3318.
14. Fanta I.W., Erman F.W. J. Org. Chem. 33:1968;1656.
15. For issues on regiochemistry on photocycloaddition of cyclic enones with allene, see: (a) Fleming, S. A.; Bradford, C. L.; Gao, J. F. In Organic Photochemistry; Ramamurthy, V.; Schanze, K. S., Eds.; Marcel Dekker: New York, 1997; pp. 187-243;
16. (b) Corey, E. J.; Bass, J. D.; LeMahieu, R.; Mitra, R. B. J. Am. Chem. Soc. 1964, 86, 5570.
17. Wender, P. A.; Glass, T. E.; Krauss, N. E.; Muhlebach, M.; Peachke, B.; Rawlins, D. B. J. Org. Chem. 1996, 61, 7662. Ozonolysis of 8 gave 4 in only 38% yield.
18. Oh-e T., Miyaura N., Suzuki A. J. Org. Chem. 58:1993;2201.
19. Griffith W.P., Ley S.V., Whitcombe G.P., White A.D. J. Chem. Soc., Chem. Commun. 1987;1625.
20. Sharpless K.B., Amberg W., Bennani Y.L., Crispino G.A., Hartung J., Jeong K.-S., Kwong H.-L., Morikawa K., Wang Z.-M., Xu D., Zhang X.-L. J. Org. Chem. 57:1992;2768.
21. Wojtowicz J.A., Polak R.J. J. Org. Chem. 38:1973;2061.