A concise enantioselective synthesis of a fully oxygen substituted ring A taxol precursor

Tetrahedron

Volumn 59, Issue 27, 2003, Pages 5115-5121

  Roy, Olivier ^a   Pattenden, Gerald ^a   Pryde, David C ^a   Wilson, Claire ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Ring A; Synthesis; Taxol

Indexed keywords

2,2 DIMETHYLCYCLOHEXAN 1,3 DIONE; CYCLOHEXANE DERIVATIVE; DOCETAXEL; PACLITAXEL; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; PRECURSOR; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0038718470     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00699-9     Document Type: Article

References (20)

1. Taxol is the registered trademark of Bristol-Myers Squibb for the generic name paclitaxel. Likewise, Taxotere is the registered trademark of Rhône-Poulenc Rorer for the generic name docetaxel.
2. (a) Nicolaou K.C., Ueno H., Liu J.-J., Nantermet P.G., Yang Z., Renaud J., Paulvannan K., Chadha R. J. Am. Chem. Soc. 117:1995;653
3. (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., Vu P., Tang S., Zhang P., Murthi K.K., Gentile L.N., Liu J.H. J. Am. Chem. Soc. 116:1994;1599
4. (c) Masters J.J., Link J.T., Snyder L.B., Young W.B., Danishefsky S.J. Angew. Chem., Int. Ed. Engl. 34:1995;1723
5. (d) Wender P.A., Badham N.F., Conway S.P., Floreancig P.E., Glass T.E., Houze J.B., Krauss N.E., Lee D., Marquess D.G., McGrane P.L., Meng W., Natchus M.G., Shuker A.J., Sutton J.C., Taylor R.E. J. Am. Chem. Soc. 119:1997;2757
6. (e) Morihara K., Hara R., Kawahara S., Nishimori T., Nakamura N., Kusama H., Kuwajima I. J. Am. Chem. Soc. 120:1998;12980
7. (f) Mukaiyama T., Shiina I., Iwadare H., Saitoh M., Nishimura T., Ohkawa N., Sakoh H., Nishimura K., Tani Y., Hasegawa M., Yamada K., Saitoh K. Chem. Eur. J. 5:1999;121.
8. For review (a) Kingston D.G.I. Chem. Commun. 2001;867
9. (b) Boa A.N., Jenkins P.R., Lawrence N.J. Contemp. Org. Synth. 1:1994;47
10. (c) Nicolaou K.C., Dai W.-M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15.
11. Hitchcock S.A., Houldsworth S.J., Pattenden G., Pryde D.C., Thomson N.M., Blake A.J. J. Chem. Soc., Perkin Trans. 1. 1998;3181.
12. Pryde, D. C. Ph.D. Thesis, University of Nottingham, 1994.
13. Di Grandi M.J., Jung D.K., Krol W.J., Danishefsky S.J. J. Org. Chem. 58:1993;4989.
14. Luche J.-L.J. J. Am. Chem. Soc. 100:1978;2226.
15. Nicolaou K.C., Liu J.-J., Yang Z., Ueno H., Sorensen E.J., Claiborne C.F., Guy R.K., Hwang C.-K., Nakada M., Nantermet P.G. J. Am. Chem. Soc. 117:1995;634.
16. (a) Shapiro R.H. Org. React. 23:1976;405
17. (b) Shapiro R.H., Heath M.J. J. Am. Chem. Soc. 89:1967;5734.
18. Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamune H., Sharpless K.B., J. J. Am. Chem. Soc. 109:1987;5765.
19. Csack N.J., Reese C.B., Risius A.C., Roozpeikar B. Tetrahedron. 32:1976;2157-2162.
20. 19F NMR of Mosher's acid derivatives Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 34:1969;2543.