A concise enantioselective pathway to carbocyclic nucleoside: Asymmetric synthesis of carbocyclic moiety of carbovir

Synthetic Communications

Volumn 27, Issue 14, 1997, Pages 2371-2378

  Tanimori, Shinji ^a   Tsubota, Masakazu ^a   He, Mingqi ^a   Nakayama, Mitsuru ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCYCLIC NUCLEOSIDE; CARBOVIR; NUCLEOSIDE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CHIRALITY; DERIVATIZATION; DRUG SYNTHESIS; ENANTIOMER; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; STEREOCHEMISTRY;

EID: 0030991875     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708004098     Document Type: Article

References (17)

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2. Vince, R. and Hua, M., J. Med. Chem., 1990, 33, 17.
3. For recent carbovir synthesis, see: Crimmins, M. T. and King, B. W., J. Org. Chem., 1996, 67, 4192, and references cited therein.
4. 3 A ring synthon, see: a) Wilson, S. R., Haque, M. S., Venkatesan, A. M., and Zucker, P. A., Tetrahedron Lett., 1984, 25, 3151; b) Nemoto, H., Wu, X.-M., Kurobe, H., Minemura, K., Ihara, M., Fukumoto, K., and Kametani, T., J. Chem. Soc., Parkin Trans. I, 1985, 1185; c) Moriarty, R. M., Kim, J., and Guo, L., Tetrahedron Lett., 1993, 34, 4129..
5. 3 A ring synthon, see: a) Wilson, S. R., Haque, M. S., Venkatesan, A. M., and Zucker, P. A., Tetrahedron Lett., 1984, 25, 3151; b) Nemoto, H., Wu, X.-M., Kurobe, H., Minemura, K., Ihara, M., Fukumoto, K., and Kametani, T., J. Chem. Soc., Parkin Trans. I, 1985, 1185; c) Moriarty, R. M., Kim, J., and Guo, L., Tetrahedron Lett., 1993, 34, 4129..
6. 3 A ring synthon, see: a) Wilson, S. R., Haque, M. S., Venkatesan, A. M., and Zucker, P. A., Tetrahedron Lett., 1984, 25, 3151; b) Nemoto, H., Wu, X.-M., Kurobe, H., Minemura, K., Ihara, M., Fukumoto, K., and Kametani, T., J. Chem. Soc., Parkin Trans. I, 1985, 1185; c) Moriarty, R. M., Kim, J., and Guo, L., Tetrahedron Lett., 1993, 34, 4129..
7. 3 A ring synthon, see: a) Wilson, S. R., Haque, M. S., Venkatesan, A. M., and Zucker, P. A., Tetrahedron Lett., 1984, 25, 3151; b) Nemoto, H., Wu, X.-M., Kurobe, H., Minemura, K., Ihara, M., Fukumoto, K., and Kametani, T., J. Chem. Soc., Parkin Trans. I, 1985, 1185; c) Moriarty, R. M., Kim, J., and Guo, L., Tetrahedron Lett., 1993, 34, 4129..
8. Enantioselective synthesis of cyclopropane 6, see: a) Taber, D. F., Amedio, Jr., J. C., and Raman, K., J. Org. Chem., 1988, 53, 2984; b) Wilson, S. R., Venkatesen, A. M., Augelli-Szafran, C. E., and Yasmin, A., Tetrahedron Lett., 1991, 32, 2339; c) ref. 4c).
9. Enantioselective synthesis of cyclopropane 6, see: a) Taber, D. F., Amedio, Jr., J. C., and Raman, K., J. Org. Chem., 1988, 53, 2984; b) Wilson, S. R., Venkatesen, A. M., Augelli-Szafran, C. E., and Yasmin, A., Tetrahedron Lett., 1991, 32, 2339; c) ref. 4c).
10. Huckin, S. N. and Weiler, L., J. Am. Chem. Soc., 1974, 96, 1082.
11. The pioneering study for pantolactone as chiral auxiliary, see: Poll, T., Sobczak, A., Hartmann, H., and Helmchen, G., Tetrahedron Lett., 1985, 26, 3095.
12. Direct conversion of methyl ester 1 to 2 by ester exchange method in the presence of 4-DMAP in PhMe at reflux for 15 h (see, ref. 5a) gave poor yield of 2 (33%, and 19% recovered).
13. Recently, Davies reported rhodium (II) catalyzed highly diastereoselective intermolecular cyclopropanation by using pantolactone as chiral auxiliary, see: Davies, H. M. L., Huby, N. J. S., Cantrell, Jr., W. R., and Olive, J. L., J. Am. Chem. Soc., 1993, 115, 9468.
14. On the other hand, when copper bronze powder was used as a catalyst, the reaction in toluene at reflux for 3 h produced 4 and 5 in a reversed ratio of 36: 64 in 43% yield.
15. The consideration of the mechanism of asymmetric induction is now under investigation.
16. 1) followed by demethoxycarbonylation in totally 38% yield from 4. But, lately, direct transformation of 4 to 10 was succeeded effectively by increasing the amount of acetic acid, elongation of reaction time, and slightly raising the reaction temperature (see experimental section).
17. Asami, M., Takahashi, J., and Inoue, S., Tetrahedron: Asymmetry, 1994, 5, 1649.