Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Syntheses of Indolizidine Alkaloids (-)-205A, (-)-207A, and (-)-235B

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 8182-8187

  Comins, Daniel L ^a   LaMunyon, Donald H ^a   Chen, Xinghai ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000690815     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971448u     Document Type: Article

References (51)

1. Reviews: (a) Suffness, M.; Cordell, G. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, FL, 1985; Vol. 25, Chapter 1, pp 3-355. (b) Gellert, E. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley & Sons: New York, 1987; Vol. 5, p 55. (c) Takahata, H.; Momose, T. In The Alkaloids' Cordell, G. A., Ed.; Academic Press, Inc.: San Diego, 1993; Vol. 44, Chapter 3. (d) Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41.
2. Reviews: (a) Suffness, M.; Cordell, G. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, FL, 1985; Vol. 25, Chapter 1, pp 3-355. (b) Gellert, E. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley & Sons: New York, 1987; Vol. 5, p 55. (c) Takahata, H.; Momose, T. In The Alkaloids' Cordell, G. A., Ed.; Academic Press, Inc.: San Diego, 1993; Vol. 44, Chapter 3. (d) Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41.
3. Reviews: (a) Suffness, M.; Cordell, G. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, FL, 1985; Vol. 25, Chapter 1, pp 3-355. (b) Gellert, E. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley & Sons: New York, 1987; Vol. 5, p 55. (c) Takahata, H.; Momose, T. In The Alkaloids' Cordell, G. A., Ed.; Academic Press, Inc.: San Diego, 1993; Vol. 44, Chapter 3. (d) Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41.
4. Reviews: (a) Suffness, M.; Cordell, G. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, FL, 1985; Vol. 25, Chapter 1, pp 3-355. (b) Gellert, E. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley & Sons: New York, 1987; Vol. 5, p 55. (c) Takahata, H.; Momose, T. In The Alkaloids' Cordell, G. A., Ed.; Academic Press, Inc.: San Diego, 1993; Vol. 44, Chapter 3. (d) Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41.
5. For recent examples of and leading references to the synthesis of indolizidine natural products see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502. (b) Okano, T.; Sakaida, T.; Eguchi, S. Heterocycles 1997, 44, 227-236. (c) Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. (d) Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G. Tetrahedron Asymmetry 1996, 7, 2211-2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H. Bioorg. Med. Chem. Lett. 1996, 6, 161-164. (g) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42.
6. For recent examples of and leading references to the synthesis of indolizidine natural products see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502. (b) Okano, T.; Sakaida, T.; Eguchi, S. Heterocycles 1997, 44, 227-236. (c) Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. (d) Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G. Tetrahedron Asymmetry 1996, 7, 2211-2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H. Bioorg. Med. Chem. Lett. 1996, 6, 161-164. (g) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42.
7. For recent examples of and leading references to the synthesis of indolizidine natural products see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502. (b) Okano, T.; Sakaida, T.; Eguchi, S. Heterocycles 1997, 44, 227-236. (c) Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. (d) Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G. Tetrahedron Asymmetry 1996, 7, 2211-2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H. Bioorg. Med. Chem. Lett. 1996, 6, 161-164. (g) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42.
8. For recent examples of and leading references to the synthesis of indolizidine natural products see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502. (b) Okano, T.; Sakaida, T.; Eguchi, S. Heterocycles 1997, 44, 227-236. (c) Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. (d) Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G. Tetrahedron Asymmetry 1996, 7, 2211-2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H. Bioorg. Med. Chem. Lett. 1996, 6, 161-164. (g) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42.
9. For recent examples of and leading references to the synthesis of indolizidine natural products see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502. (b) Okano, T.; Sakaida, T.; Eguchi, S. Heterocycles 1997, 44, 227-236. (c) Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. (d) Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G. Tetrahedron Asymmetry 1996, 7, 2211-2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H. Bioorg. Med. Chem. Lett. 1996, 6, 161-164. (g) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42.
10. For recent examples of and leading references to the synthesis of indolizidine natural products see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502. (b) Okano, T.; Sakaida, T.; Eguchi, S. Heterocycles 1997, 44, 227-236. (c) Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. (d) Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G. Tetrahedron Asymmetry 1996, 7, 2211-2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H. Bioorg. Med. Chem. Lett. 1996, 6, 161-164. (g) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42.
11. For recent examples of and leading references to the synthesis of indolizidine natural products see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502. (b) Okano, T.; Sakaida, T.; Eguchi, S. Heterocycles 1997, 44, 227-236. (c) Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. (d) Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G. Tetrahedron Asymmetry 1996, 7, 2211-2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H. Bioorg. Med. Chem. Lett. 1996, 6, 161-164. (g) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42.
12. For recent examples of and leading references to the synthesis of indolizidine natural products see: (a) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, pp 453-502. (b) Okano, T.; Sakaida, T.; Eguchi, S. Heterocycles 1997, 44, 227-236. (c) Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. (d) Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G. Tetrahedron Asymmetry 1996, 7, 2211-2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H. Bioorg. Med. Chem. Lett. 1996, 6, 161-164. (g) Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42.
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28. A similar stereoselective transformation has been reported, see: (a) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. Tetrahedron Lett. 1992, 33, 7635. (b) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732. (c) ref 4a.
29. A similar stereoselective transformation has been reported, see: (a) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. Tetrahedron Lett. 1992, 33, 7635. (b) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732. (c) ref 4a.
30. A similar stereoselective transformation has been reported, see: (a) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. Tetrahedron Lett. 1992, 33, 7635. (b) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732. (c) ref 4a.
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43. For enantioselective syntheses of these indolizidines, see: (a) (-)-205A, (-)-235B: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. Shishido, Y.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1991, 1237. (b) (-)-205A, (-)-207A, (-)-235B: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. (d) (-)-207A, (-)-235B: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943; Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553. (e) (-)-207A: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529. (f) Also, for the first synthesis of a 5,8-disubstituted indolizidine ((-)-209B), see: Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
44. For enantioselective syntheses of these indolizidines, see: (a) (-)-205A, (-)-235B: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. Shishido, Y.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1991, 1237. (b) (-)-205A, (-)-207A, (-)-235B: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. (d) (-)-207A, (-)-235B: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943; Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553. (e) (-)-207A: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529. (f) Also, for the first synthesis of a 5,8-disubstituted indolizidine ((-)-209B), see: Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
45. For enantioselective syntheses of these indolizidines, see: (a) (-)-205A, (-)-235B: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. Shishido, Y.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1991, 1237. (b) (-)-205A, (-)-207A, (-)-235B: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. (d) (-)-207A, (-)-235B: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943; Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553. (e) (-)-207A: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529. (f) Also, for the first synthesis of a 5,8-disubstituted indolizidine ((-)-209B), see: Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
46. For enantioselective syntheses of these indolizidines, see: (a) (-)-205A, (-)-235B: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. Shishido, Y.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1991, 1237. (b) (-)-205A, (-)-207A, (-)-235B: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. (d) (-)-207A, (-)-235B: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943; Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553. (e) (-)-207A: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529. (f) Also, for the first synthesis of a 5,8-disubstituted indolizidine ((-)-209B), see: Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
47. For enantioselective syntheses of these indolizidines, see: (a) (-)-205A, (-)-235B: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. Shishido, Y.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1991, 1237. (b) (-)-205A, (-)-207A, (-)-235B: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. (d) (-)-207A, (-)-235B: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943; Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553. (e) (-)-207A: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529. (f) Also, for the first synthesis of a 5,8-disubstituted indolizidine ((-)-209B), see: Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
48. For enantioselective syntheses of these indolizidines, see: (a) (-)-205A, (-)-235B: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. Shishido, Y.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1991, 1237. (b) (-)-205A, (-)-207A, (-)-235B: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. (d) (-)-207A, (-)-235B: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943; Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553. (e) (-)-207A: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529. (f) Also, for the first synthesis of a 5,8-disubstituted indolizidine ((-)-209B), see: Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
49. For enantioselective syntheses of these indolizidines, see: (a) (-)-205A, (-)-235B: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. Shishido, Y.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1991, 1237. (b) (-)-205A, (-)-207A, (-)-235B: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. (d) (-)-207A, (-)-235B: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943; Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553. (e) (-)-207A: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529. (f) Also, for the first synthesis of a 5,8-disubstituted indolizidine ((-)-209B), see: Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
50. For enantioselective syntheses of these indolizidines, see: (a) (-)-205A, (-)-235B: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. Shishido, Y.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1991, 1237. (b) (-)-205A, (-)-207A, (-)-235B: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. (d) (-)-207A, (-)-235B: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943; Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553. (e) (-)-207A: Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529. (f) Also, for the first synthesis of a 5,8-disubstituted indolizidine ((-)-209B), see: Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Swithenbank, C.; Lidert, Z. J. Am. Chem. Soc. 1988, 110, 8696.
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