Synthesis of Enantiopure Indolizidine Alkaloids from α-Amino Acids: Total Synthesis of (-)-Indolizidine 167B

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8549-8552

  Angle, Steven R ^a   Henry, Robert M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000193858     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970591k     Document Type: Article

References (53)

1. For leading references to the biological activity of indolizidine alkaloids, see: (a) Michael, J. P. Nat Prod. Rep. 1997, 14, 21-41. (b) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press, Inc.: San Diego, 1993; Vol. 44, Chapter 3.
2. For leading references to the biological activity of indolizidine alkaloids, see: (a) Michael, J. P. Nat Prod. Rep. 1997, 14, 21-41. (b) Takahata, H.; Momose, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press, Inc.: San Diego, 1993; Vol. 44, Chapter 3.
3. 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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
4. 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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
13. 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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
14. 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; Stereoselectiue 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. Comins, D. L.; Zhang, Y. M. J. Am. Chem. Soc. 1996, 118, 12248-12249. Michael, J. P.; Gravestock, D. Synlett 1996, 981-982. (e) Thanh, G. V.; Célérier, J.-P.; Lhommet, 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.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708. (h) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39-42. Muraoka, O.; Zheng, B-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc., Perkin Trans. 1, 1997, 113-119. (j) Lee, E.; Kang, T.; Chung, C. Bull. Korean Chem. Soc. 1996, 17, 212-214. (k) Solladié, G.; Chu, G.-H. Tetrahedron Lett. 1996, 37, 111-114. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400.
15. (a) Angle, S. R.; Breitenbucher, J. G.; Arnaiz, D. O. J. Org. Chem. 1992, 57, 5947-5955.
16. (b) Angle, S. R.; Arnaiz, D. O. Tetrahedron Lett. 1989, 30, 515-518.
17. Angle, S. R.; Breitenbucher, J. G. Tetrahedron Lett. 1993, 34, 3985-3988.
18. For the detection of (-)-indolizidine 167B see: Daly, J. W. Fortschr. Chem. Org. Naturst. 1982, 41, 205-340.
19. (a) Daly, J. W.; Myers, C. W.; Whittaker, N. Toxicon 1987, 25, 1023-1095.
20. (b) Tokuyama, T.; Nishimori, N.; Karle, I. L.; Edwards, M. W.; Daly, J. W. Tetrahedron 1986, 42, 3453-3460.
21. Daly, J. W.; Spanade, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4, Chapter 1.
22. Daly, J. W.; Secunda, S. I.; Garraffo, H. M.; Spande, T. F.; Wisnieski, A.; Cover Jr., J. F. Toxicon 1994, 32, 657-663.
23. For leading references and previous synthesis of (±)-indolizidine167B see: (a) Holmes, A. B.; Smith, A. L.; Williams, S. F.; Hughes, L. R.; Lidert, Z.; Swithenbank, C. J. Org. Chem. 1991, 56, 1393-1405. (b) Zeller, E.; Sajus, H.; Grierson, D. S. Synlett 1991, 44-46. Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Lidert, Z.; Swithenbank, C. J. Am. Chem. Soc. 1988, 110, 8696-8698.
24. For leading references and previous synthesis of (±)-indolizidine167B see: (a) Holmes, A. B.; Smith, A. L.; Williams, S. F.; Hughes, L. R.; Lidert, Z.; Swithenbank, C. J. Org. Chem. 1991, 56, 1393-1405. (b) Zeller, E.; Sajus, H.; Grierson, D. S. Synlett 1991, 44-46. Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Lidert, Z.; Swithenbank, C. J. Am. Chem. Soc. 1988, 110, 8696-8698.
25. For leading references and previous synthesis of (±)-indolizidine167B see: (a) Holmes, A. B.; Smith, A. L.; Williams, S. F.; Hughes, L. R.; Lidert, Z.; Swithenbank, C. J. Org. Chem. 1991, 56, 1393-1405. (b) Zeller, E.; Sajus, H.; Grierson, D. S. Synlett 1991, 44-46. Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Lidert, Z.; Swithenbank, C. J. Am. Chem. Soc. 1988, 110, 8696-8698.
26. For previous synthesis of (+)- and (-)-indolizidine167B see: (a) Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445-1446. (b) (+)-167B: Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797-1804. Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W. K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119-3122. (e) Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron Asymmetry 1992, 3, 695-696. (f) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688-4693.
27. For previous synthesis of (+)- and (-)-indolizidine167B see: (a) Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445-1446. (b) (+)-167B: Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797-1804. Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W. K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119-3122. (e) Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron Asymmetry 1992, 3, 695-696. (f) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688-4693.
28. For previous synthesis of (+)- and (-)-indolizidine167B see: (a) Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445-1446. (b) (+)-167B: Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797-1804. Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W. K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119-3122. (e) Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron Asymmetry 1992, 3, 695-696. (f) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688-4693.
29. For previous synthesis of (+)- and (-)-indolizidine167B see: (a) Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445-1446. (b) (+)-167B: Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797-1804. Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W. K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119-3122. (e) Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron Asymmetry 1992, 3, 695-696. (f) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688-4693.
30. For previous synthesis of (+)- and (-)-indolizidine167B see: (a) Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445-1446. (b) (+)-167B: Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797-1804. Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W. K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119-3122. (e) Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron Asymmetry 1992, 3, 695-696. (f) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688-4693.
31. For previous synthesis of (+)- and (-)-indolizidine167B see: (a) Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445-1446. (b) (+)-167B: Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797-1804. Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W. K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119-3122. (e) Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron Asymmetry 1992, 3, 695-696. (f) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688-4693.
32. For leading references to other examples of conformationally restricted Claisen rearrangements see: (a) Danishefsky, S. J.; Audia, J. E. Tetrahedron Lett. 1988, 29, 1371-1374. (b) Burke, S. D.; Armistead, D. M.; Schoenen, F. J. J. Org. Chem. 1984, 49, 4320-4322. Burke, S. D.; Schoenen, F. J.; Murtiashaw, C. W. Tetrahedron Lett. 1986, 27, 449-452. Büchi, G.; Powell, J. E., Jr. J. Am. Chem. Soc. 1970, 92, 3126-3133. (e) Kang, H.-J.; Paquette, L. A. J. Am. Chem. Soc. 1990, 112, 3252-3253.
33. For leading references to other examples of conformationally restricted Claisen rearrangements see: (a) Danishefsky, S. J.; Audia, J. E. Tetrahedron Lett. 1988, 29, 1371-1374. (b) Burke, S. D.; Armistead, D. M.; Schoenen, F. J. J. Org. Chem. 1984, 49, 4320-4322. Burke, S. D.; Schoenen, F. J.; Murtiashaw, C. W. Tetrahedron Lett. 1986, 27, 449-452. Büchi, G.; Powell, J. E., Jr. J. Am. Chem. Soc. 1970, 92, 3126-3133. (e) Kang, H.-J.; Paquette, L. A. J. Am. Chem. Soc. 1990, 112, 3252-3253.
34. For leading references to other examples of conformationally restricted Claisen rearrangements see: (a) Danishefsky, S. J.; Audia, J. E. Tetrahedron Lett. 1988, 29, 1371-1374. (b) Burke, S. D.; Armistead, D. M.; Schoenen, F. J. J. Org. Chem. 1984, 49, 4320-4322. Burke, S. D.; Schoenen, F. J.; Murtiashaw, C. W. Tetrahedron Lett. 1986, 27, 449-452. Büchi, G.; Powell, J. E., Jr. J. Am. Chem. Soc. 1970, 92, 3126-3133. (e) Kang, H.-J.; Paquette, L. A. J. Am. Chem. Soc. 1990, 112, 3252-3253.
35. For leading references to other examples of conformationally restricted Claisen rearrangements see: (a) Danishefsky, S. J.; Audia, J. E. Tetrahedron Lett. 1988, 29, 1371-1374. (b) Burke, S. D.; Armistead, D. M.; Schoenen, F. J. J. Org. Chem. 1984, 49, 4320-4322. Burke, S. D.; Schoenen, F. J.; Murtiashaw, C. W. Tetrahedron Lett. 1986, 27, 449-452. Büchi, G.; Powell, J. E., Jr. J. Am. Chem. Soc. 1970, 92, 3126-3133. (e) Kang, H.-J.; Paquette, L. A. J. Am. Chem. Soc. 1990, 112, 3252-3253.
36. For leading references to other examples of conformationally restricted Claisen rearrangements see: (a) Danishefsky, S. J.; Audia, J. E. Tetrahedron Lett. 1988, 29, 1371-1374. (b) Burke, S. D.; Armistead, D. M.; Schoenen, F. J. J. Org. Chem. 1984, 49, 4320-4322. Burke, S. D.; Schoenen, F. J.; Murtiashaw, C. W. Tetrahedron Lett. 1986, 27, 449-452. Büchi, G.; Powell, J. E., Jr. J. Am. Chem. Soc. 1970, 92, 3126-3133. (e) Kang, H.-J.; Paquette, L. A. J. Am. Chem. Soc. 1990, 112, 3252-3253.
37. (a) Breitenbucher, J. G., Ph.D. Dissertation, University of California at Riverside, 1993.
38. (b) Boyce, J. P., Ph.D. Dissertation, University of California at Riverside, 1994.
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41. (a) Synthesis of norvaline ethyl ester: Titouani, S. L.; Lavergne, J. P.; Viallefont, PH. Tetrahedron 1980, 36, 2961-2965. (b) Rotation and alternative synthesis of L-(+)-norvaline ethyl ester: Fu, S.-C. J.; Birnbaum, S. M.; Greenstein, J. P. J. Am. Chem. Soc. 1954, 76, 6054-6058. Synthesis of N-benzoyl D-norvaline ethyl ester: Karrer, V. P.; Schneider, H. Helv. Chim Acta 1930, 13, 1281-1291.
42. (a) Synthesis of norvaline ethyl ester: Titouani, S. L.; Lavergne, J. P.; Viallefont, PH. Tetrahedron 1980, 36, 2961-2965. (b) Rotation and alternative synthesis of L-(+)-norvaline ethyl ester: Fu, S.-C. J.; Birnbaum, S. M.; Greenstein, J. P. J. Am. Chem. Soc. 1954, 76, 6054-6058. Synthesis of N-benzoyl D-norvaline ethyl ester: Karrer, V. P.; Schneider, H. Helv. Chim Acta 1930, 13, 1281-1291.
43. (a) Synthesis of norvaline ethyl ester: Titouani, S. L.; Lavergne, J. P.; Viallefont, PH. Tetrahedron 1980, 36, 2961-2965. (b) Rotation and alternative synthesis of L-(+)-norvaline ethyl ester: Fu, S.-C. J.; Birnbaum, S. M.; Greenstein, J. P. J. Am. Chem. Soc. 1954, 76, 6054-6058. Synthesis of N-benzoyl D-norvaline ethyl ester: Karrer, V. P.; Schneider, H. Helv. Chim Acta 1930, 13, 1281-1291.
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49. Corey, E. J.; Smith, J. G.; J. Am. Chem. Soc. 1979, 101, 1038-1039. Similar problems with a palladium-catalyzed hydrogenation following a Swern oxidation have been reported: Kocienski, P. J. Protecting Groups; George Thieme Verlag: New York, 1994; p 137.
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52. 13C NMR spectra, MS data, and rotation to that reported for the natural product.
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