Practical synthesis of spirocyclic bis-C,C-glycosides. Mechanistic models in explanation of rearrangement stereoselectivity and the bifurcation of reaction pathways

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1713-1722

  Paquette, Leo A ^a   Kinney, Margaret J ^a   Dullweber, Uta ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; DRUG STABILITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0030894227     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962020i     Document Type: Article

References (59)

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30. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
31. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
32. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
33. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
34. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
35. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
36. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
37. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
38. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
39. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
40. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
41. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
42. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
43. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
44. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
45. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
46. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
47. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
48. Relevant examples include the following, (a) Danishefsky, S.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3803. (b) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360. (c) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J.; Golik, J.; Vyas, D. J. Org. Chem. 1990, 55, 1979. (d) Dawe, R. D.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1981, 1180. (e) Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1992, 33, 7911. (f) Tsukiyama, T.; Peters, S. C.; Isobe, M. Synlett 1993, 413. (g) Valverde, S.; Garcia-Ochoa, S.; Martin-Lomas, M. J. Chem. Soc., Chem. Commun. 1987, 383. (h) Borowiecka, J.; Lipka, P.; Michalska, M. Tetrahedron 1988, 44, 2067. (i) Frappa, L; Sinou, D. Synth. Commun. 1995, 25, 2941. (j) Pérez-Pérez, M.-J.; Doboszewski, B.; Rozenski, J.; Herdewijn, P. Tetrahedron: Asymmetry 1995, 6, 973. (k) Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714. (l) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757. (m) Booma, C.; Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. 1993, 1394. (n) Nakata, M.; Tamai, T.; Miura, Y.; Kinoshita, M.; Tatsuta, K. J. Antibiot. 1993, 46, 813. (o) Paterson, I.; Smith, J. D.; Ward, R. A. Tetrahedron 1995, 51, 9413. (p) Noshita, T.; Sugiyama, T.; Kitazumi, Y.; Oritani, T. Tetrahedron Lett. 1994, 35, 8259. (q) López, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 3851. (r) López, J. C.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1992, 94. (s) Fraser-Reid, Tsang, R. Strategies and Tactics in Organic Synthesis; Academic Press Inc.: New York, 1989.
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59. The authors have deposited the atomic coordinates for the X-ray structures 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, U.K.