Biomimetic entry to the sarpagan family of indole alkaloids: Total synthesis of (+)-geissoschizine and (+)-N-methylvellosimine

Journal of the American Chemical Society

Volumn 125, Issue 15, 2003, Pages 4541-4550

  Deiters, Alexander ^a   Chen, Kevin ^a   Eary, C Todd ^a   Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PRECURSORS;

AMINO ACIDS; BIOMIMETIC MATERIALS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

AJMALINE; ALKALOID DERIVATIVE; CARBOLINE DERIVATIVE; CARBOXYL GROUP; ETHER DERIVATIVE; GEISSOSCHIZINE; INDOLE ALKALOID; LACTAM; N METHYLVELLOSIMINE; SARPAGINE ALKALOID; SILYL ETHER; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; BIOSYNTHESIS; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOSELECTIVITY; IONIZATION; MANNICH REACTION; STEREOCHEMISTRY;

BIOMIMETIC MATERIALS; CARBOLINES; INDOLE ALKALOIDS; STEREOISOMERISM;

EID: 0037448898     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0296024     Document Type: Article

References (94)

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39. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
40. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
41. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
42. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
43. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
44. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
45. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
46. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
47. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
48. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
49. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
50. Syntheses of racemic geissoschizine: (a) Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E. J. Chem. Soc., Chem. Commun. 1974, 908. (b) Hachmeister, B.; Thielke, D.; Winterfeldt, E. Chem. Ber. 1976, 109, 3825. (c) Wenkert, E.; Vankar, Y. D.; Yadav, J. S. J. Am. Chem. Soc. 1980, 102. 7971. (d) Banks, B. J.; Calverley, M. J.; Edwards, P. D.; Harley-Mason, J. Tetrahedron Lett. 1981, 22, 1631. (e) Martin, S. F.; Benage, B.; Hunter. J. E. J. Am. Chem. Soc. 1988, 110, 5925. (f) Wenkert, E.; Guo, M.; Pesthanker, M. J.; Shi, Y. J.; Vanker, Y. D. J. Org. Chem. 1989, 54, 1166. (g) Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161. (h) Lounasmaa, M.; Jokela, R.; Miettinen, J.; Halonen, M. Heterocycles 1992, 34, 1497. (i) Lounasmaa, M.; Jokela, R.; Anttila, U.; Hanhinen, P.; Laine, C. Tetrahedron 1996, 52, 6803. (j) Bennasar, M.-L.; Jimenez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105. (k) Takayama, H.; Watanabe, F.; Kitajima, M.; Aimi, N. Tetrahedron Lett. 1997, 38, 5307. (l) Bennasar, M.-L.; Jimenez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
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