A Novel and Highly Stereoselective Approach to Aza-Spirocycles. A Short Total Synthesis of 2-epi-(±)-Perhydrohistrionicotoxin and an Unprecedented Decarboxylation of 2-Pyrones

Organic Letters

Volumn 4, Issue 12, 2002, Pages 2017-2020

  McLaughlin, Michael J ^a   Hsung, Richard P ^a   Cole, Kevin P ^a   Hahn, Juliet M ^a   Wang, Jiashi ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIBIAN VENOM; CARBOXYLIC ACID; HETEROCYCLIC COMPOUND; PERHYDROHISTRIONICOTOXIN; PYRONE DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMPHIBIAN VENOMS; AZA COMPOUNDS; CARBOXYLIC ACIDS; PYRONES; STEREOISOMERISM;

EID: 0037071942     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020052o     Document Type: Article

References (50)

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41. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
42. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
43. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
44. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
45. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
46. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
47. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
48. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
49. For recent efforts in total synthesis of perhydrohistrionicotoxin or histrionicotoxin, see: (a) Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B.; Adams, J. P. J. Am. Chem. Soc. 1999, 121, 4900. (b) Comins, D. L.; Zhang, Y.-M.; Zheng, X. J. Chem. Soc., Chem. Commun. 1998, 2509. (c) Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907. (d) Comins, D. L.; Zheng, X. J. Chem. Soc., Chem. Commun. 1994, 2681. (e) Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875. (f) Winkler, J. D.; Hershberger, P. M. J. Am. Chem. Soc. 1989, 111, 4852. (g) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374. (h) Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B. J. Org. Chem. 1989, 54, 4419. For the first synthesis of (±)-histrionicotoxin, see: (i) Carey, S. C.; Aratani, M.; Kishi, Y. Tetrahedron Lett. 1985, 26, 5887.
50. For matching the characterization 2-epi-(±)-perhydrohistrionicotoxin, see: Takahashi, K.; Wiktop, B.; Brossi, A.; Maleque, M. A.; Albuquerque, E. X. Helv. Chim. Acta 1982, 6, 252.