Synthetic efforts toward akuammiline alkaloids from tetracyclic 6,7-seco derivatives

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1239-1250

  Bennasar, M Lluïsa ^a   Zulaica, Ester ^a   Ramírez, Antonio ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029911562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951456f     Document Type: Article

References (82)

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7. These structural variations have been chemically correlated with the akuammiline alkaloids: see ref 1.
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24. Carbanion nucleophile additions to N-alkyl-β-acylpyridinium salts for alkaloid synthesis were first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Quo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and references cited therein. For a review, see (c) Bennasar, M.-L., Lavilla, R.; Alvarez, M.; Bosch, J. Heterocycles 1988, 27, 789. For more recent work, see (d) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (e) Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156. (f) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320. (g) Bennasar, M.-L.; Zulaica, E.; Bosch, J. J. Org. Chem. 1992, 57, 2835. (h) Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340. (i) Bennasar, M.-L.; Vidai, B.; Bosch, J J. Chem. Soc., Chem. Commun. 1995, 125.
25. Carbanion nucleophile additions to N-alkyl-β-acylpyridinium salts for alkaloid synthesis were first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Quo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and references cited therein. For a review, see (c) Bennasar, M.-L., Lavilla, R.; Alvarez, M.; Bosch, J. Heterocycles 1988, 27, 789. For more recent work, see (d) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (e) Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156. (f) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320. (g) Bennasar, M.-L.; Zulaica, E.; Bosch, J. J. Org. Chem. 1992, 57, 2835. (h) Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340. (i) Bennasar, M.-L.; Vidai, B.; Bosch, J J. Chem. Soc., Chem. Commun. 1995, 125.
26. Carbanion nucleophile additions to N-alkyl-β-acylpyridinium salts for alkaloid synthesis were first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Quo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and references cited therein. For a review, see (c) Bennasar, M.-L., Lavilla, R.; Alvarez, M.; Bosch, J. Heterocycles 1988, 27, 789. For more recent work, see (d) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (e) Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156. (f) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320. (g) Bennasar, M.-L.; Zulaica, E.; Bosch, J. J. Org. Chem. 1992, 57, 2835. (h) Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340. (i) Bennasar, M.-L.; Vidai, B.; Bosch, J J. Chem. Soc., Chem. Commun. 1995, 125.
27. Carbanion nucleophile additions to N-alkyl-β-acylpyridinium salts for alkaloid synthesis were first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Quo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and references cited therein. For a review, see (c) Bennasar, M.-L., Lavilla, R.; Alvarez, M.; Bosch, J. Heterocycles 1988, 27, 789. For more recent work, see (d) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (e) Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156. (f) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320. (g) Bennasar, M.-L.; Zulaica, E.; Bosch, J. J. Org. Chem. 1992, 57, 2835. (h) Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340. (i) Bennasar, M.-L.; Vidai, B.; Bosch, J J. Chem. Soc., Chem. Commun. 1995, 125.
28. Carbanion nucleophile additions to N-alkyl-β-acylpyridinium salts for alkaloid synthesis were first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Quo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and references cited therein. For a review, see (c) Bennasar, M.-L., Lavilla, R.; Alvarez, M.; Bosch, J. Heterocycles 1988, 27, 789. For more recent work, see (d) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (e) Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156. (f) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320. (g) Bennasar, M.-L.; Zulaica, E.; Bosch, J. J. Org. Chem. 1992, 57, 2835. (h) Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340. (i) Bennasar, M.-L.; Vidai, B.; Bosch, J J. Chem. Soc., Chem. Commun. 1995, 125.
29. Carbanion nucleophile additions to N-alkyl-β-acylpyridinium salts for alkaloid synthesis were first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Quo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and references cited therein. For a review, see (c) Bennasar, M.-L., Lavilla, R.; Alvarez, M.; Bosch, J. Heterocycles 1988, 27, 789. For more recent work, see (d) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (e) Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156. (f) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320. (g) Bennasar, M.-L.; Zulaica, E.; Bosch, J. J. Org. Chem. 1992, 57, 2835. (h) Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340. (i) Bennasar, M.-L.; Vidai, B.; Bosch, J J. Chem. Soc., Chem. Commun. 1995, 125.
30. Carbanion nucleophile additions to N-alkyl-β-acylpyridinium salts for alkaloid synthesis were first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Quo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and references cited therein. For a review, see (c) Bennasar, M.-L., Lavilla, R.; Alvarez, M.; Bosch, J. Heterocycles 1988, 27, 789. For more recent work, see (d) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (e) Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156. (f) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320. (g) Bennasar, M.-L.; Zulaica, E.; Bosch, J. J. Org. Chem. 1992, 57, 2835. (h) Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340. (i) Bennasar, M.-L.; Vidai, B.; Bosch, J J. Chem. Soc., Chem. Commun. 1995, 125.
31. Carbanion nucleophile additions to N-alkyl-β-acylpyridinium salts for alkaloid synthesis were first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Quo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and references cited therein. For a review, see (c) Bennasar, M.-L., Lavilla, R.; Alvarez, M.; Bosch, J. Heterocycles 1988, 27, 789. For more recent work, see (d) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (e) Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156. (f) Amann, R.; Spitzner, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1320. (g) Bennasar, M.-L.; Zulaica, E.; Bosch, J. J. Org. Chem. 1992, 57, 2835. (h) Bennasar, M.-L.; Vidai, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340. (i) Bennasar, M.-L.; Vidai, B.; Bosch, J J. Chem. Soc., Chem. Commun. 1995, 125.
32. For previous syntheses of ABDE substructures of akuammiline alkaloids, see (a) Bosch, J.; Mauleón, D.; Feliz, M.; Granados, R. J. Org. Chem. 1983, 48, 4836. (b) Bosch, J.; Feliz, M.; Bennasar, M.-L. Tetrahedron 1984, 40, 1419. (c) Salas, M.; Joule, J. J. Chem. Res. (M) 1990, 664. See also ref 8b.
33. For previous syntheses of ABDE substructures of akuammiline alkaloids, see (a) Bosch, J.; Mauleón, D.; Feliz, M.; Granados, R. J. Org. Chem. 1983, 48, 4836. (b) Bosch, J.; Feliz, M.; Bennasar, M.-L. Tetrahedron 1984, 40, 1419. (c) Salas, M.; Joule, J. J. Chem. Res. (M) 1990, 664. See also ref 8b.
34. For previous syntheses of ABDE substructures of akuammiline alkaloids, see (a) Bosch, J.; Mauleón, D.; Feliz, M.; Granados, R. J. Org. Chem. 1983, 48, 4836. (b) Bosch, J.; Feliz, M.; Bennasar, M.-L. Tetrahedron 1984, 40, 1419. (c) Salas, M.; Joule, J. J. Chem. Res. (M) 1990, 664. See also ref 8b.
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