Diastereo- and enantioselective synthesis of allylsilane. A useful C-ring fragment of taxol

Tetrahedron Letters

Volumn 38, Issue 23, 1997, Pages 4129-4132

  Kusama, Hiroyuki ^a   Mori, Takeshi ^a   Mitani, Ikuo ^a   Kashima, Hajime ^a   Kuwajima, Isao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PACLITAXEL; SILANE DERIVATIVE; TAXANE DERIVATIVE;

ARTICLE; CONFORMATION; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; STEREOISOMERISM;

EID: 0030917765     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00843-5     Document Type: Article

References (20)

1. a) Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186-9187.
2. b) Seto, M.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. J. Org. Chem. 1994, 59, 3165-3174.
3. Fleming, I.; Dunogues, J.; Smithers, R. Org. Reactions 37, 57-575 (1989).
4. Nakamura, T.; Waizumi, N.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1994, 35, 7813-7816.
5. a) Horiguchi, Y.; Furukawa, T.; Kuwajima, I. J. Am. Chem. Soc. 1989, III, 8277-8279.
6. b) Furukawa, T.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. Tetrahedron 1992, 48, 6975-6978.
7. a) Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021-9024.
8. b) Marumoto, S.; Kuwajima, I. Chem. Lett. 1992, 1421-1424.
9. For the preparation of the pyrone 3, see: Jung, M. E. In Strategies and Tactics in Organic Synthesis; Lindberg, T. Ed; Academic Press, Inc.; San Diego, 1989; Vol. 2, p. 250.
10. On enantioselective [4 + 2] cycloaddition of pyrones induced by chiral Lewis acids, a) Posner, G. H.; Carry, J.-C.; Lee, J. K.; Bull, D. S.; Dai, H. Tetrahedron Lett. 1994, 35, 1321-1324.
11. b) Markó, I. E.; Evans, G. R. ibid. 1994, 35, 2767-2770.
12. c) Markó, I. E.; Evans, G. R. ibid. 1994, 35, 2771-2774.
13. d) Markó, I. E.; Evans, G. R. Synlett 1994, 431-433.
14. e) Posner, G. H.; Eydoux, F.; Lee, J. K.; Bull, D. S. Tetrahedron Lett. 1994, 35, 7541-7544.
15. f) Posner, G. H.; Carry, J.-C.; Anjeh, T. E. N.; French, A. N. J. Org. Chem. 1992, 57, 7012-7014.
16. On diastereoselective reactions of pyrones using chiral vinyl ether, a) Posner. G. H.; Wettlaufer, D. G. Tetrahedron Lett. 1986, 27, 667-670.
17. b) Posner, G. H.; Kinter, C. M. J. Org. Chem. 1990, 55, 3967-3969.
18. 1H-NMR analysis of the corresponding (+)-MTPA ester.
19. The absolute configuration of this compound was determined by X-ray crystallographic analysis.
20. Stereochemical feature of this compound was determined by NOE experiments described in the text.