Asymmetric synthesis of tetracyclic substructures of Strychnos indole alkaloids

Tetrahedron Asymmetry

Volumn 14, Issue 12, 2003, Pages 1691-1699

  Amat, Mercedes ^a   Coll, M Dolors ^a   Llor, Núria ^a   Escolano, Carmen ^a   Molins, Elies ^b   Miravitlles, Carles ^b   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARBOXYLIC ACID DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; INDOLE DERIVATIVE; INDOLEACETIC ACID DERIVATIVE; INORGANIC SALT; LITHIUM 2 (LITHIOMETHYL)INDOLE 1 CARBOXYLATE; METHYL 1 METHYL 2 INDOLEACETATE; N ALKYLPYRIDINIUM; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037867663     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00251-9     Document Type: Article

References (38)

1. For reviews, see: (a) Sapi, J.; Massiot, G. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Supplement to Vol. 25, Part 4, Chapter 7; (b) Bosch, J.; Bonjoch, J.; Amat, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996; Vol. 48, pp. 75-189; (c) Bonjoch, J.; Solé, D. Chem. Rev. 2000, 100, 3455-3482.
2. For reviews, see: (a) Sapi, J.; Massiot, G. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Supplement to Vol. 25, Part 4, Chapter 7; (b) Bosch, J.; Bonjoch, J.; Amat, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996; Vol. 48, pp. 75-189; (c) Bonjoch, J.; Solé, D. Chem. Rev. 2000, 100, 3455-3482.
3. For reviews, see: (a) Sapi, J.; Massiot, G. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Supplement to Vol. 25, Part 4, Chapter 7; (b) Bosch, J.; Bonjoch, J.; Amat, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996; Vol. 48, pp. 75-189; (c) Bonjoch, J.; Solé, D. Chem. Rev. 2000, 100, 3455-3482.
4. Biogenetic numbering: Le Men J., Taylor W.I. Experientia. 21:1965;508-510.
5. For precedents of this key cyclization (in the racemic series), see: (a) Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299-6312; (b) Gràcia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1994, 59, 3939-3951.
6. For precedents of this key cyclization (in the racemic series), see: (a) Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299-6312; (b) Gràcia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1994, 59, 3939-3951.
7. For a recent review on the chemistry of dihydropyridines, see: Lavilla R. J. Chem. Soc., Perkin Trans. 1. 2002;1141-1156.
8. For the generation of enantiopure 1,4-dihydropyridines by addition of organometallic reagents to pyridines and pyridinium salts bearing a chiral auxiliary at the 3-position of the ring, see: (a) Meyers, A. I.; Natale, N. R.; Wettlaufer, D. G.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1981, 22, 5123-5126; (b) Meyers, A. I.; Oppenlaender, T. J. Chem. Soc., Chem. Commun. 1986, 920-921; (c) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1986; (d) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; (e) Raussou, S.; Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M. Tetrahedron Lett. 1994, 35, 5433-5436; (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949; (g) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185; (h) Yamada, S.; Saitoh, M.; Misono, T. Tetrahedron Lett. 2002, 43, 5853-5857.
9. For the generation of enantiopure 1,4-dihydropyridines by addition of organometallic reagents to pyridines and pyridinium salts bearing a chiral auxiliary at the 3-position of the ring, see: (a) Meyers, A. I.; Natale, N. R.; Wettlaufer, D. G.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1981, 22, 5123-5126; (b) Meyers, A. I.; Oppenlaender, T. J. Chem. Soc., Chem. Commun. 1986, 920-921; (c) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1986; (d) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; (e) Raussou, S.; Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M. Tetrahedron Lett. 1994, 35, 5433-5436; (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949; (g) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185; (h) Yamada, S.; Saitoh, M.; Misono, T. Tetrahedron Lett. 2002, 43, 5853-5857.
10. For the generation of enantiopure 1,4-dihydropyridines by addition of organometallic reagents to pyridines and pyridinium salts bearing a chiral auxiliary at the 3-position of the ring, see: (a) Meyers, A. I.; Natale, N. R.; Wettlaufer, D. G.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1981, 22, 5123-5126; (b) Meyers, A. I.; Oppenlaender, T. J. Chem. Soc., Chem. Commun. 1986, 920-921; (c) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1986; (d) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; (e) Raussou, S.; Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M. Tetrahedron Lett. 1994, 35, 5433-5436; (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949; (g) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185; (h) Yamada, S.; Saitoh, M.; Misono, T. Tetrahedron Lett. 2002, 43, 5853-5857.
11. For the generation of enantiopure 1,4-dihydropyridines by addition of organometallic reagents to pyridines and pyridinium salts bearing a chiral auxiliary at the 3-position of the ring, see: (a) Meyers, A. I.; Natale, N. R.; Wettlaufer, D. G.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1981, 22, 5123-5126; (b) Meyers, A. I.; Oppenlaender, T. J. Chem. Soc., Chem. Commun. 1986, 920-921; (c) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1986; (d) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; (e) Raussou, S.; Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M. Tetrahedron Lett. 1994, 35, 5433-5436; (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949; (g) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185; (h) Yamada, S.; Saitoh, M.; Misono, T. Tetrahedron Lett. 2002, 43, 5853-5857.
12. For the generation of enantiopure 1,4-dihydropyridines by addition of organometallic reagents to pyridines and pyridinium salts bearing a chiral auxiliary at the 3-position of the ring, see: (a) Meyers, A. I.; Natale, N. R.; Wettlaufer, D. G.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1981, 22, 5123-5126; (b) Meyers, A. I.; Oppenlaender, T. J. Chem. Soc., Chem. Commun. 1986, 920-921; (c) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1986; (d) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; (e) Raussou, S.; Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M. Tetrahedron Lett. 1994, 35, 5433-5436; (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949; (g) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185; (h) Yamada, S.; Saitoh, M.; Misono, T. Tetrahedron Lett. 2002, 43, 5853-5857.
13. For the generation of enantiopure 1,4-dihydropyridines by addition of organometallic reagents to pyridines and pyridinium salts bearing a chiral auxiliary at the 3-position of the ring, see: (a) Meyers, A. I.; Natale, N. R.; Wettlaufer, D. G.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1981, 22, 5123-5126; (b) Meyers, A. I.; Oppenlaender, T. J. Chem. Soc., Chem. Commun. 1986, 920-921; (c) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1986; (d) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; (e) Raussou, S.; Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M. Tetrahedron Lett. 1994, 35, 5433-5436; (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949; (g) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185; (h) Yamada, S.; Saitoh, M.; Misono, T. Tetrahedron Lett. 2002, 43, 5853-5857.
14. For the generation of enantiopure 1,4-dihydropyridines by addition of organometallic reagents to pyridines and pyridinium salts bearing a chiral auxiliary at the 3-position of the ring, see: (a) Meyers, A. I.; Natale, N. R.; Wettlaufer, D. G.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1981, 22, 5123-5126; (b) Meyers, A. I.; Oppenlaender, T. J. Chem. Soc., Chem. Commun. 1986, 920-921; (c) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1986; (d) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; (e) Raussou, S.; Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M. Tetrahedron Lett. 1994, 35, 5433-5436; (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949; (g) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185; (h) Yamada, S.; Saitoh, M.; Misono, T. Tetrahedron Lett. 2002, 43, 5853-5857.
15. For the generation of enantiopure 1,4-dihydropyridines by addition of organometallic reagents to pyridines and pyridinium salts bearing a chiral auxiliary at the 3-position of the ring, see: (a) Meyers, A. I.; Natale, N. R.; Wettlaufer, D. G.; Rafii, S.; Clardy, J. Tetrahedron Lett. 1981, 22, 5123-5126; (b) Meyers, A. I.; Oppenlaender, T. J. Chem. Soc., Chem. Commun. 1986, 920-921; (c) Meyers, A. I.; Oppenlaender, T. J. Am. Chem. Soc. 1986, 108, 1989-1986; (d) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888; (e) Raussou, S.; Gosmini, R.; Mangeney, P.; Alexakis, A.; Commerçon, M. Tetrahedron Lett. 1994, 35, 5433-5436; (f) Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. Tetrahedron 2001, 57, 8939-8949; (g) Yamada, S.; Morita, C. J. Am. Chem. Soc. 2002, 124, 8184-8185; (h) Yamada, S.; Saitoh, M.; Misono, T. Tetrahedron Lett. 2002, 43, 5853-5857.
16. For the generation of enantiopure tetracyclic ABDE substructures of Strychnos alkaloids using this methodology from a chiral non-racemic 3-(oxazolinyl)pyridine, see: Amat, M.; Coll, M.-D.; Bosch, J. Tetrahedron 1995, 39, 10759-10770.
17. For a review, see: (a) Bosch, J.; Bennasar, M.-L. Synlett 1995, 587-596. For more recent work, see: (b) Bennasar, M.-L.; Jiménez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605-9612; (c) Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597-3609; (d) Bennasar, M.-L.; Vidal, B.; Kumar, R.; Lázaro, A.; Bosch, J. Eur. J. Org. Chem. 2000, 3919-3925.
18. For a review, see: (a) Bosch, J.; Bennasar, M.-L. Synlett 1995, 587-596. For more recent work, see: (b) Bennasar, M.-L.; Jiménez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605-9612; (c) Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597-3609; (d) Bennasar, M.-L.; Vidal, B.; Kumar, R.; Lázaro, A.; Bosch, J. Eur. J. Org. Chem. 2000, 3919-3925.
19. For a review, see: (a) Bosch, J.; Bennasar, M.-L. Synlett 1995, 587-596. For more recent work, see: (b) Bennasar, M.-L.; Jiménez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605-9612; (c) Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597-3609; (d) Bennasar, M.-L.; Vidal, B.; Kumar, R.; Lázaro, A.; Bosch, J. Eur. J. Org. Chem. 2000, 3919-3925.
20. For a review, see: (a) Bosch, J.; Bennasar, M.-L. Synlett 1995, 587-596. For more recent work, see: (b) Bennasar, M.-L.; Jiménez, J.-M.; Vidal, B.; Sufi, B. A.; Bosch, J. J. Org. Chem. 1999, 64, 9605-9612; (c) Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597-3609; (d) Bennasar, M.-L.; Vidal, B.; Kumar, R.; Lázaro, A.; Bosch, J. Eur. J. Org. Chem. 2000, 3919-3925.
21. (a) Bennasar, M.-L.; Zulaica, E.; Alonso, Y.; Bosch. J. Tetrahedron: Asymmetry 2003, 14, 469-479.
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23. (c) Amann, R.; Arnold, K.; Spitzner, D.; Majer, Z.; Snatzke, G. Liebigs Ann. 1996, 349-355;
24. (d) Bennasar, M.-L.; Zulaica, E.; Alonso, Y.; Vidal, B.; Vázquez, J. T.; Bosch, J. Tetrahedron: Asymmetry 2002, 13, 95-106.
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28. 6 cis/trans isomers shifted to 4:1 for rac-3 and 7:3 for rac-3′ when the temperature during the nucleophilic addition was allowed to rise to -10°C
29. For previous use of this criteria, see Ref. 10.
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31. For reviews, see: (a) Davies, S. G. Pure Appl. Chem. 1988, 60, 13-20; (b) Davies, S. G. Aldrichimica Acta 1990, 23, 31-37.
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36. This kind of ring opening has previously been observed: Wenkert W., Angell C., Drexler J., Moeller P.D.R., Pyrek J.S., Shi Y.-J., Sultana M., Vankar Y.D. J. Org. Chem. 51:1986;2995-3000. see also Ref. 10.
37. 2 in 13a). For 13a this ratio shifted to 1:1 when the temperature during the nucleophilic addition was allowed to rise to +10°C.
38. -3. Calculations were done using the WinGX package (Farrugia, L. J. J. Appl. Cryst. 1999, 32, 837-838).