Allylic substitution of 3′,4′-unsaturated nucleosides: Organosilicon-based stereoselective access to 4′-C-branched 2′,3′-didehydro-2′,3′-dideoxyribonucleosides

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 851-858

  Haraguchi, Kazuhiro ^a   Tanaka, Hiromichi ^a   Itoh, Yoshiharu ^a   Yamaguchi, Kentaro ^a,b   Miyasaka, Tadashi ^a  

^a SHOWA UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEHYDRO 2',3' DIDEOXYNUCLEOSIDE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030046801     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9516190     Document Type: Article

References (58)

1. For the synthesis of 4′,5′-unsaturated nucleosides: (a) Verheyden, J. P. H.; Moffatt, J. G. J. Am. Chem. Soc. 1966, 88, 5684-5685. (b) Robins, M. J.; McCarthy, J. R., Jr.; Robins, R. K. J. Heterocycl. Chem. 1967, 4, 313-314. (c) Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem. 1974, 39, 3573-3579.
2. For the synthesis of 4′,5′-unsaturated nucleosides: (a) Verheyden, J. P. H.; Moffatt, J. G. J. Am. Chem. Soc. 1966, 88, 5684-5685. (b) Robins, M. J.; McCarthy, J. R., Jr.; Robins, R. K. J. Heterocycl. Chem. 1967, 4, 313-314. (c) Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem. 1974, 39, 3573-3579.
3. For the synthesis of 4′,5′-unsaturated nucleosides: (a) Verheyden, J. P. H.; Moffatt, J. G. J. Am. Chem. Soc. 1966, 88, 5684-5685. (b) Robins, M. J.; McCarthy, J. R., Jr.; Robins, R. K. J. Heterocycl. Chem. 1967, 4, 313-314. (c) Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem. 1974, 39, 3573-3579.
4. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
5. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
6. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
7. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
8. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
9. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
10. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
11. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
12. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
13. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
14. For the synthesis of 2′,3′-unsaturated nucleosides: (a) Horwitz, J. P.; Chua, J.; Klundt, I. L.; Da Rooge, M. A.; Noel, M. J. Am. Chem. Soc. 1964, 86, 1896-1897. (b) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M. Tetrahedron Lett. 1964, 2725-2727. (c) Ruyle, W. V.; Shen, T. Y.; Patchett, A. A. J. Org. Chem. 1965, 30, 4353-4355. (d) Horwitz, J. P.; Chua, J.; Da Rooge, M. A.; Noel, M.; Klundt, I. L. J Org. Chem. 1966, 31, 205-211. (e) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1967, 10, 1066-1070. (f) Khwaja, T. A.; Heidelberger, C. J. Med. Chem. 1969, 12, 543-545. (g) Kowollik, G., Gaertner, K.; Etzold, G.; Langen, P. Carbohydr. Res. 1970, 12, 301-311. (h) Robins, M. J.; Hansske, F.; Low, N. H.; Park, J. I. Tetrahedron Lett. 1984, 25, 367-370. (i) Cosford, N. D. P.; Schinazi, R. F. J. Org. Chem. 1991, 56, 2161-2165. (j) Talekar, R. R.; Coe, P. L.; Walker, R. T. Synthesis 1993, 303-306. (k) Cosford, N. D. P.; Schinazi, R. F. Nucleosides Nucleotides 1993, 12, 149-155.
15. For the synthesis of 1′,2′-unsaturated nucleosides: (a) Robins, M. J.; Trip, E. M. Tetrahedron Lett. 1974, 3369-3372. (b) Ranganathan, R. Tetrahedron Lett. 1977, 1291-1294.
16. For the synthesis of 1′,2′-unsaturated nucleosides: (a) Robins, M. J.; Trip, E. M. Tetrahedron Lett. 1974, 3369-3372. (b) Ranganathan, R. Tetrahedron Lett. 1977, 1291-1294.
17. For the synthesis of 3′,4′-unsaturated nucleosides: (a) Zemlicka, J.; Freisler, J. V.; Gasser, R.; Horwitz, J. P. J. Org. Chem. 1973, 38, 990-999. (b) Lichtenthaler, F. W.; Kitahara, K.; Strobel, K. Synthesis 1974, 860-862. (c) Herdewijn, P.; Ruf, K.; Pfleiderer, W Helv. Chim. Acta 1991, 74, 7-23.
18. For the synthesis of 3′,4′-unsaturated nucleosides: (a) Zemlicka, J.; Freisler, J. V.; Gasser, R.; Horwitz, J. P. J. Org. Chem. 1973, 38, 990-999. (b) Lichtenthaler, F. W.; Kitahara, K.; Strobel, K. Synthesis 1974, 860-862. (c) Herdewijn, P.; Ruf, K.; Pfleiderer, W Helv. Chim. Acta 1991, 74, 7-23.
19. For the synthesis of 3′,4′-unsaturated nucleosides: (a) Zemlicka, J.; Freisler, J. V.; Gasser, R.; Horwitz, J. P. J. Org. Chem. 1973, 38, 990-999. (b) Lichtenthaler, F. W.; Kitahara, K.; Strobel, K. Synthesis 1974, 860-862. (c) Herdewijn, P.; Ruf, K.; Pfleiderer, W Helv. Chim. Acta 1991, 74, 7-23.
20. 2F, and COOH): (a) Nagpal, K. L.; Horwitz, J. P. J. Org. Chem. 1971, 36, 3743-3745. (b) Kowellik, G.; Gaertner, K.; Langen. P. Tetrahedron Lett. 1971, 1737-1740. (c) Zemlicka, J.; Gasser, R.; Freisler, J. V.; Horwitz, J P. J Am. Chem. Soc. 1972, 94, 3213-3218.
21. 2F, and COOH): (a) Nagpal, K. L.; Horwitz, J. P. J. Org. Chem. 1971, 36, 3743-3745. (b) Kowellik, G.; Gaertner, K.; Langen. P. Tetrahedron Lett. 1971, 1737-1740. (c) Zemlicka, J.; Gasser, R.; Freisler, J. V.; Horwitz, J P. J Am. Chem. Soc. 1972, 94, 3213-3218.
22. 2F, and COOH): (a) Nagpal, K. L.; Horwitz, J. P. J. Org. Chem. 1971, 36, 3743-3745. (b) Kowellik, G.; Gaertner, K.; Langen. P. Tetrahedron Lett. 1971, 1737-1740. (c) Zemlicka, J.; Gasser, R.; Freisler, J. V.; Horwitz, J P. J Am. Chem. Soc. 1972, 94, 3213-3218.
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49. Reactions between glycals and trialkylaluminum with allylic substitution have been reported: Maruoka, K.; Nonoshita, K.; Itoh, T.; Yamamoto, H. Chem. Lett. 1987, 2215-2216.
50. 2O: C, 66.57; H, 5 92; N, 6.21. Found: C, 66.76; H, 5.88; N, 6.22.
51. 2 gave a similar result, forming 11b in 25% yield as well as 12b (24%) and 13b (12%).
52. The author has deposited atomic coordinates for 12a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
53. Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
54. Compounds 18 and 19 consist of two isomers about the α-carbon of the 1-oxocyclopent-2-yl moiety.
55. The stereochemistry of 20 and 21 about the 2′-position is not known.
56. Yamaguchi, K.; Haraguchi, K.; Tanaka, H.; Itoh, Y.; Miyasaka, T. Acta Crystallogr. 1992, C48, 2277-2278.
57. 2O addition, is assignable to H-2.
58. 4 (0.2 equiv) in THF. No reaction took place at room temperature, and heating of the reaction mixture at 60 °C overnight gave the corresponding furan derivative (20%) along with the recovered 9b (32%).