Chemo-, Regio-, and Enantioselective Pd-Catalyzed Allylic Alkylation of Indolocarbazole Pro-aglycons

Organic Letters

Volumn 4, Issue 12, 2002, Pages 2005-2008

  Trost, Barry M ^a   Krische, Michael J ^a   Berl, Volker ^a   Grenzer, Ellen M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKYLATION; CARBAZOLES; CATALYSIS; INDOLES; PALLADIUM; STEREOISOMERISM;

EID: 0037071923     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020046s     Document Type: Article

References (41)

1. For reviews on studies related to their chemistry and biology, see: Gribble, G.; Berthel, S. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1993; Vol. 12, p 365. Sapi, J.; Massiot, G. The Alkaloids; Academic Press: New York, 1995; Vol. 47, p 173. Bergman, J. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1988; Vol. 1, p 3. Steglich, W. Pure Appl. Chem. 1989, 61, 281. For a review on the bioactivity of staurosporine, see: Omura, S.; Sasaki, Y.; Iwai, Y.; Takeshima, H. J. Antibiot. 1995, 48, 535.
2. For reviews on studies related to their chemistry and biology, see: Gribble, G.; Berthel, S. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1993; Vol. 12, p 365. Sapi, J.; Massiot, G. The Alkaloids; Academic Press: New York, 1995; Vol. 47, p 173. Bergman, J. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1988; Vol. 1, p 3. Steglich, W. Pure Appl. Chem. 1989, 61, 281. For a review on the bioactivity of staurosporine, see: Omura, S.; Sasaki, Y.; Iwai, Y.; Takeshima, H. J. Antibiot. 1995, 48, 535.
3. For reviews on studies related to their chemistry and biology, see: Gribble, G.; Berthel, S. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1993; Vol. 12, p 365. Sapi, J.; Massiot, G. The Alkaloids; Academic Press: New York, 1995; Vol. 47, p 173. Bergman, J. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1988; Vol. 1, p 3. Steglich, W. Pure Appl. Chem. 1989, 61, 281. For a review on the bioactivity of staurosporine, see: Omura, S.; Sasaki, Y.; Iwai, Y.; Takeshima, H. J. Antibiot. 1995, 48, 535.
4. For reviews on studies related to their chemistry and biology, see: Gribble, G.; Berthel, S. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1993; Vol. 12, p 365. Sapi, J.; Massiot, G. The Alkaloids; Academic Press: New York, 1995; Vol. 47, p 173. Bergman, J. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1988; Vol. 1, p 3. Steglich, W. Pure Appl. Chem. 1989, 61, 281. For a review on the bioactivity of staurosporine, see: Omura, S.; Sasaki, Y.; Iwai, Y.; Takeshima, H. J. Antibiot. 1995, 48, 535.
5. For reviews on studies related to their chemistry and biology, see: Gribble, G.; Berthel, S. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1993; Vol. 12, p 365. Sapi, J.; Massiot, G. The Alkaloids; Academic Press: New York, 1995; Vol. 47, p 173. Bergman, J. Studies in Natural Products Chemistry; Elsevier Science Publishers: New York, 1988; Vol. 1, p 3. Steglich, W. Pure Appl. Chem. 1989, 61, 281. For a review on the bioactivity of staurosporine, see: Omura, S.; Sasaki, Y.; Iwai, Y.; Takeshima, H. J. Antibiot. 1995, 48, 535.
6. (a) Sarstedt, B.; Winterfeldt, E. Heterocycles 1983, 20, 469.
7. (b) Hughes, I.; Nolan, W. P.; Raphael, R. A. J. Chem. Soc., Perkin Trans. 1 1990, 2475.
8. (c) Moody, C. J.; Rahimtoola, K. F. Chem. Soc., Chem. Commun. 1990, 1667.
9. (d) Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555.
10. Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552; Link, J. T.; Danishefsky, S. J. Tetrahedron Lett. 1994, 35, 9131.
11. Link, J. T.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552; Link, J. T.; Danishefsky, S. J. Tetrahedron Lett. 1994, 35, 9131.
12. (c) Link, J. T.; Danishefsky, S. J. Tetrahedron Lett. 1994, 35, 9135. Link, J. T.; Raghavan, S.; Gallant, M.; Chou, T. C.; Ballas, L. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 2825.
13. (c) Link, J. T.; Danishefsky, S. J. Tetrahedron Lett. 1994, 35, 9135. Link, J. T.; Raghavan, S.; Gallant, M.; Chou, T. C.; Ballas, L. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 2825.
14. Wood, J.; Stolz, B. M.; Dietrich, H.-J. J. Am. Chem. Soc. 1995, 117, 10413.
15. Wood, J. L.; Petsch, D. T.; Stoltz, B. M.; Hawkins, E. M.; Elbaum, D.; Stover, D. R. Synthesis 1999, 1529. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. J. Am. Chem. Soc. 1997, 119, 9652. Wood, J. L.; Stoltz, B. M.; Dietrich, H. J.; Pflum, D. A.; Petsch, D. T.. J. Am. Chem. Soc. 1997, 119, 9641. Wood, J. L.; Stoltz, B. M.; Goodman, S. N. J. Am. Chem. Soc. 1996, 118, 10656. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. Tetrahedron Lett. 1996, 37, 7335.
16. Wood, J. L.; Petsch, D. T.; Stoltz, B. M.; Hawkins, E. M.; Elbaum, D.; Stover, D. R. Synthesis 1999, 1529. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. J. Am. Chem. Soc. 1997, 119, 9652. Wood, J. L.; Stoltz, B. M.; Dietrich, H. J.; Pflum, D. A.; Petsch, D. T.. J. Am. Chem. Soc. 1997, 119, 9641. Wood, J. L.; Stoltz, B. M.; Goodman, S. N. J. Am. Chem. Soc. 1996, 118, 10656. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. Tetrahedron Lett. 1996, 37, 7335.
17. Wood, J. L.; Petsch, D. T.; Stoltz, B. M.; Hawkins, E. M.; Elbaum, D.; Stover, D. R. Synthesis 1999, 1529. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. J. Am. Chem. Soc. 1997, 119, 9652. Wood, J. L.; Stoltz, B. M.; Dietrich, H. J.; Pflum, D. A.; Petsch, D. T.. J. Am. Chem. Soc. 1997, 119, 9641. Wood, J. L.; Stoltz, B. M.; Goodman, S. N. J. Am. Chem. Soc. 1996, 118, 10656. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. Tetrahedron Lett. 1996, 37, 7335.
18. Wood, J. L.; Petsch, D. T.; Stoltz, B. M.; Hawkins, E. M.; Elbaum, D.; Stover, D. R. Synthesis 1999, 1529. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. J. Am. Chem. Soc. 1997, 119, 9652. Wood, J. L.; Stoltz, B. M.; Dietrich, H. J.; Pflum, D. A.; Petsch, D. T.. J. Am. Chem. Soc. 1997, 119, 9641. Wood, J. L.; Stoltz, B. M.; Goodman, S. N. J. Am. Chem. Soc. 1996, 118, 10656. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. Tetrahedron Lett. 1996, 37, 7335.
19. Wood, J. L.; Petsch, D. T.; Stoltz, B. M.; Hawkins, E. M.; Elbaum, D.; Stover, D. R. Synthesis 1999, 1529. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. J. Am. Chem. Soc. 1997, 119, 9652. Wood, J. L.; Stoltz, B. M.; Dietrich, H. J.; Pflum, D. A.; Petsch, D. T.. J. Am. Chem. Soc. 1997, 119, 9641. Wood, J. L.; Stoltz, B. M.; Goodman, S. N. J. Am. Chem. Soc. 1996, 118, 10656. Wood, J. L.; Stoltz, B. M.; Goodman, S. N.; Onwneme, K. Tetrahedron Lett. 1996, 37, 7335.
20. (e) Stoltz, B. M.; Wood, J. L. Tetrahedron Lett. 1996, 37, 3925.
21. Gilbert, E. J.; Ziller, J. W.; Van Vranken, D. L. Tetrahedron 1997, 53, 16553. Gilbert, E. J.; Vanvranken, D. L. J. Am. Chem. Soc. 1996, 118, 5500.
22. Gilbert, E. J.; Ziller, J. W.; Van Vranken, D. L. Tetrahedron 1997, 53, 16553. Gilbert, E. J.; Vanvranken, D. L. J. Am. Chem. Soc. 1996, 118, 5500.
23. Eils, S.; Winterfeldt, E. Synthesis 1999, 275. Riley, D. A.; Simpkins, N. S.; Moffat, D. Tetrahedron Lett. 1999, 40, 3929. Royer, H.; Joseph, D.; Prim, D.; Kirsch, G. Synth. Commun. 1998, 28, 1239. Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Ito, S.; Morishima, H. Tetrahedron 1997, 53, 5937. Merlic, C. A.; McInnes, D. M. Tetrahedron Lett. 1997, 38, 7661. Merlic, C. A.; McInnes, D. M.; You, Y. Tetrahedron Lett. 1997, 38, 6787.
24. Eils, S.; Winterfeldt, E. Synthesis 1999, 275. Riley, D. A.; Simpkins, N. S.; Moffat, D. Tetrahedron Lett. 1999, 40, 3929. Royer, H.; Joseph, D.; Prim, D.; Kirsch, G. Synth. Commun. 1998, 28, 1239. Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Ito, S.; Morishima, H. Tetrahedron 1997, 53, 5937. Merlic, C. A.; McInnes, D. M. Tetrahedron Lett. 1997, 38, 7661. Merlic, C. A.; McInnes, D. M.; You, Y. Tetrahedron Lett. 1997, 38, 6787.
25. Eils, S.; Winterfeldt, E. Synthesis 1999, 275. Riley, D. A.; Simpkins, N. S.; Moffat, D. Tetrahedron Lett. 1999, 40, 3929. Royer, H.; Joseph, D.; Prim, D.; Kirsch, G. Synth. Commun. 1998, 28, 1239. Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Ito, S.; Morishima, H. Tetrahedron 1997, 53, 5937. Merlic, C. A.; McInnes, D. M. Tetrahedron Lett. 1997, 38, 7661. Merlic, C. A.; McInnes, D. M.; You, Y. Tetrahedron Lett. 1997, 38, 6787.
26. Eils, S.; Winterfeldt, E. Synthesis 1999, 275. Riley, D. A.; Simpkins, N. S.; Moffat, D. Tetrahedron Lett. 1999, 40, 3929. Royer, H.; Joseph, D.; Prim, D.; Kirsch, G. Synth. Commun. 1998, 28, 1239. Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Ito, S.; Morishima, H. Tetrahedron 1997, 53, 5937. Merlic, C. A.; McInnes, D. M. Tetrahedron Lett. 1997, 38, 7661. Merlic, C. A.; McInnes, D. M.; You, Y. Tetrahedron Lett. 1997, 38, 6787.
27. Eils, S.; Winterfeldt, E. Synthesis 1999, 275. Riley, D. A.; Simpkins, N. S.; Moffat, D. Tetrahedron Lett. 1999, 40, 3929. Royer, H.; Joseph, D.; Prim, D.; Kirsch, G. Synth. Commun. 1998, 28, 1239. Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Ito, S.; Morishima, H. Tetrahedron 1997, 53, 5937. Merlic, C. A.; McInnes, D. M. Tetrahedron Lett. 1997, 38, 7661. Merlic, C. A.; McInnes, D. M.; You, Y. Tetrahedron Lett. 1997, 38, 6787.
28. Eils, S.; Winterfeldt, E. Synthesis 1999, 275. Riley, D. A.; Simpkins, N. S.; Moffat, D. Tetrahedron Lett. 1999, 40, 3929. Royer, H.; Joseph, D.; Prim, D.; Kirsch, G. Synth. Commun. 1998, 28, 1239. Ohkubo, M.; Nishimura, T.; Jona, H.; Honma, T.; Ito, S.; Morishima, H. Tetrahedron 1997, 53, 5937. Merlic, C. A.; McInnes, D. M. Tetrahedron Lett. 1997, 38, 7661. Merlic, C. A.; McInnes, D. M.; You, Y. Tetrahedron Lett. 1997, 38, 6787.
29. Kobayashi, Y.; Fujimoto, T.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 6501
30. Trost, B. M.; VanVranken, D. L. Chem. Rev. 1996, 96, 395.
31. Trost, B. M.; Van Vranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228.
32. The good yields obtained in the cyclopentenylation reactions were found to be crucially dependent on careful oxygen exclusion from the reaction vessels.
33. Systematic conformational searches were performed with the computer program CAChe Workstation Plus DGauss (Ver. 4.4), using molecular mechanics with augmented MM3 parameter sets. Subsequent geometric optimization using semiempirical PM3 potential functions.
34. For the calculation of equilibrium constants, the computer program CHEM-EQUILI (Ver. 6.1) was employed. For a detailed description, see: Solov'ev, V. P.; Vnuk, E. A.; Strakhova, N. N.; Raevsky, O. A. Thermodynamic of complexation of the macrocyclic polyethers with salts of alkali and alkaline-earth metals: VINITI: Moscow, 1991.
35. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089.
36. (b) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. J. Am. Chem. Soc. 1992, 114, 9327.
37. Exclusive nucleophilic attack on the π-allylpalladium complex terminus proximal to the oxygen of the pyran was supported by NMR chemical shift and coupling constant analyses.
38. (a) Joyce, R.; Gainor, J.; Weinreb, S. M. J. Org. Chem. 1987, 52, 1177.
39. (b) Link, J. T.; Raghaven, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552.
40. For precedence on the improvement of ee employing L2 instead of L1, see: Trost, B. M.; Schroeder, G. M. J. Org. Chem. 2000, 65, 1569.
41. Structure factors available from author upon request.