Palladium-catalyzed enantioselective synthesis of carbanucleosides

Journal of the American Chemical Society

Volumn 122, Issue 25, 2000, Pages 5947-5956

  Trost, Barry M ^a   Madsen, Robert ^a   Guile, Simon D ^a   Brown, Brian ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ARISTEROMYCIN; CARBOVIR; CYCLOPENTENE DERIVATIVE; GUANINE DERIVATIVE; METHYL GROUP; NEPLANOCIN A; NUCLEIC ACID BASE; NUCLEOSIDE DERIVATIVE; PALLADIUM; SULFONE DERIVATIVE;

ALKYLATION; AMINATION; ARTICLE; CATALYSIS; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ISOMERISM; LIGAND BINDING; STEREOCHEMISTRY;

EID: 0034725386     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9938837     Document Type: Article

References (73)

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14. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
15. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
16. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
17. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
18. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
19. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
20. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
21. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
22. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
23. For previous syntheses of (-)-carbovir, see: (a) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391. (b) Martínez, L. E.; Nugent, W. A.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 7963. (c) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192. (d) Hildbrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236. (e) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649. (h) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745. (i) Evans, C. T.; Roberts, S. M.; Shoberu, K. A.; Sutherland, A. G. J. Chem. Soc., Perkin Trans. 1 1992, 589. (j) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990. (k) Jones, M. F.; Myers, P. L.; Robertson, C. A.; Storer, R.; Williamson, C. J. Chem. Soc., Perkin Trans. 1 1991, 2479.
24. For previous syntheses of (-)-aristeromycin, see: (a) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976. (b) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247. (c) Csuk, R.; Dörr, P. Tetrahedron 1995, 51, 5789. (d) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (e) Yoshikawa, M.; Okaichi, Y.; Cha, B. C.; Kitagawa, I. Tetrahedron 1990, 46, 7459. (f) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712. (g) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049. (h) Also see: refs 9b and 9h as well as Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Woloo, J. A.; McCarthy, N. R. Bioorg. Med. Chem. Lett. 1993, 3, 165.
25. For previous syntheses of (-)-aristeromycin, see: (a) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976. (b) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247. (c) Csuk, R.; Dörr, P. Tetrahedron 1995, 51, 5789. (d) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (e) Yoshikawa, M.; Okaichi, Y.; Cha, B. C.; Kitagawa, I. Tetrahedron 1990, 46, 7459. (f) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712. (g) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049. (h) Also see: refs 9b and 9h as well as Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Woloo, J. A.; McCarthy, N. R. Bioorg. Med. Chem. Lett. 1993, 3, 165.
26. For previous syntheses of (-)-aristeromycin, see: (a) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976. (b) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247. (c) Csuk, R.; Dörr, P. Tetrahedron 1995, 51, 5789. (d) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (e) Yoshikawa, M.; Okaichi, Y.; Cha, B. C.; Kitagawa, I. Tetrahedron 1990, 46, 7459. (f) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712. (g) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049. (h) Also see: refs 9b and 9h as well as Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Woloo, J. A.; McCarthy, N. R. Bioorg. Med. Chem. Lett. 1993, 3, 165.
27. For previous syntheses of (-)-aristeromycin, see: (a) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976. (b) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247. (c) Csuk, R.; Dörr, P. Tetrahedron 1995, 51, 5789. (d) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (e) Yoshikawa, M.; Okaichi, Y.; Cha, B. C.; Kitagawa, I. Tetrahedron 1990, 46, 7459. (f) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712. (g) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049. (h) Also see: refs 9b and 9h as well as Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Woloo, J. A.; McCarthy, N. R. Bioorg. Med. Chem. Lett. 1993, 3, 165.
28. For previous syntheses of (-)-aristeromycin, see: (a) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976. (b) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247. (c) Csuk, R.; Dörr, P. Tetrahedron 1995, 51, 5789. (d) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (e) Yoshikawa, M.; Okaichi, Y.; Cha, B. C.; Kitagawa, I. Tetrahedron 1990, 46, 7459. (f) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712. (g) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049. (h) Also see: refs 9b and 9h as well as Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Woloo, J. A.; McCarthy, N. R. Bioorg. Med. Chem. Lett. 1993, 3, 165.
29. For previous syntheses of (-)-aristeromycin, see: (a) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976. (b) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247. (c) Csuk, R.; Dörr, P. Tetrahedron 1995, 51, 5789. (d) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (e) Yoshikawa, M.; Okaichi, Y.; Cha, B. C.; Kitagawa, I. Tetrahedron 1990, 46, 7459. (f) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712. (g) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049. (h) Also see: refs 9b and 9h as well as Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Woloo, J. A.; McCarthy, N. R. Bioorg. Med. Chem. Lett. 1993, 3, 165.
30. For previous syntheses of (-)-aristeromycin, see: (a) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976. (b) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247. (c) Csuk, R.; Dörr, P. Tetrahedron 1995, 51, 5789. (d) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (e) Yoshikawa, M.; Okaichi, Y.; Cha, B. C.; Kitagawa, I. Tetrahedron 1990, 46, 7459. (f) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712. (g) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049. (h) Also see: refs 9b and 9h as well as Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Woloo, J. A.; McCarthy, N. R. Bioorg. Med. Chem. Lett. 1993, 3, 165.
31. For previous syntheses of (-)-aristeromycin, see: (a) Boyer, S. J.; Leahy, J. W. J. Org. Chem. 1997, 62, 3976. (b) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247. (c) Csuk, R.; Dörr, P. Tetrahedron 1995, 51, 5789. (d) Tanaka, M.; Yoshioka, M.; Sakai, K. J. Chem. Soc., Chem. Commun. 1992, 1454. (e) Yoshikawa, M.; Okaichi, Y.; Cha, B. C.; Kitagawa, I. Tetrahedron 1990, 46, 7459. (f) Wolfe, M. S.; Anderson, B. L.; Borcherding, D. R.; Borchardt, R. T. J. Org. Chem. 1990, 55, 4712. (g) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049. (h) Also see: refs 9b and 9h as well as Matthews, D. P.; Edwards, M. L.; Mehdi, S.; Koehl, J. R.; Woloo, J. A.; McCarthy, N. R. Bioorg. Med. Chem. Lett. 1993, 3, 165.
32. For previous syntheses of (-)-neplanocin A, see: (a) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677. (b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621. (c) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537. (d) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1483. (e) Vanhessche, K.; Bello, C. G.; Vandewalle, M. Synlett 1991, 921. (f) Bestmann, H. J.; Roth, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 99. (g) Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709. (h) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131 and refs 10f and 10g.
33. For previous syntheses of (-)-neplanocin A, see: (a) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677. (b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621. (c) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537. (d) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1483. (e) Vanhessche, K.; Bello, C. G.; Vandewalle, M. Synlett 1991, 921. (f) Bestmann, H. J.; Roth, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 99. (g) Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709. (h) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131 and refs 10f and 10g.
34. For previous syntheses of (-)-neplanocin A, see: (a) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677. (b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621. (c) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537. (d) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1483. (e) Vanhessche, K.; Bello, C. G.; Vandewalle, M. Synlett 1991, 921. (f) Bestmann, H. J.; Roth, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 99. (g) Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709. (h) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131 and refs 10f and 10g.
35. For previous syntheses of (-)-neplanocin A, see: (a) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677. (b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621. (c) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537. (d) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1483. (e) Vanhessche, K.; Bello, C. G.; Vandewalle, M. Synlett 1991, 921. (f) Bestmann, H. J.; Roth, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 99. (g) Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709. (h) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131 and refs 10f and 10g.
36. For previous syntheses of (-)-neplanocin A, see: (a) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677. (b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621. (c) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537. (d) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1483. (e) Vanhessche, K.; Bello, C. G.; Vandewalle, M. Synlett 1991, 921. (f) Bestmann, H. J.; Roth, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 99. (g) Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709. (h) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131 and refs 10f and 10g.
37. For previous syntheses of (-)-neplanocin A, see: (a) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677. (b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621. (c) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537. (d) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1483. (e) Vanhessche, K.; Bello, C. G.; Vandewalle, M. Synlett 1991, 921. (f) Bestmann, H. J.; Roth, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 99. (g) Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709. (h) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131 and refs 10f and 10g.
38. For previous syntheses of (-)-neplanocin A, see: (a) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677. (b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621. (c) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537. (d) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1483. (e) Vanhessche, K.; Bello, C. G.; Vandewalle, M. Synlett 1991, 921. (f) Bestmann, H. J.; Roth, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 99. (g) Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709. (h) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131 and refs 10f and 10g.
39. For previous syntheses of (-)-neplanocin A, see: (a) Yoshida, N.; Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1998, 39, 4677. (b) Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621. (c) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537. (d) Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M.; Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. 1 1994, 1483. (e) Vanhessche, K.; Bello, C. G.; Vandewalle, M. Synlett 1991, 921. (f) Bestmann, H. J.; Roth, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 99. (g) Marquez, V. E.; Lim, M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709. (h) Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131 and refs 10f and 10g.
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58. For some recent examples, see: Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755; Zhang, D.; Ghosh, A.; Süling, C.; Miller, M. J. Tetrahedron Lett. 1996, 37, 3799; Popescu, A.; Hornfeldt, A.-B.; Gronowitz, S.; Johansson, N. G. Nucleosides Nucleotides 1995, 14, 1639; and ref 10b. Cieplak effect has been proposed as an explanation for this unusual selectivity, see: Katagiri, N.; Ito, Y.; Kitano, K.; Toyota, A.; Kaneko, C. Chem. Pharm. Bull. 1994, 42, 2653; Palmer, C. F.; McCague, R.; Ruecroft, G.; Savage, S.; Taylor, S. J. C.; Ries, C. Tetrahedron Lett. 1996, 37, 4601.
59. For some recent examples, see: Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755; Zhang, D.; Ghosh, A.; Süling, C.; Miller, M. J. Tetrahedron Lett. 1996, 37, 3799; Popescu, A.; Hornfeldt, A.-B.; Gronowitz, S.; Johansson, N. G. Nucleosides Nucleotides 1995, 14, 1639; and ref 10b. Cieplak effect has been proposed as an explanation for this unusual selectivity, see: Katagiri, N.; Ito, Y.; Kitano, K.; Toyota, A.; Kaneko, C. Chem. Pharm. Bull. 1994, 42, 2653; Palmer, C. F.; McCague, R.; Ruecroft, G.; Savage, S.; Taylor, S. J. C.; Ries, C. Tetrahedron Lett. 1996, 37, 4601.
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66. 34 As a result, we believe the structure of this reported intermediate in the previous neplanocin synthesis is in fact the C-4′ epimer of 46.
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