A Concise and Convergent Route to 5,8-Disubstituted Indolizidine and 1,4-Disubstituted Quinolizidine Ring Cores by Diastereoselective Aza-Diels-Alder Reaction

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1971-1974

  Barluenga, José ^a   Mateos, Carlos ^a   Aznar, Fernando ^a   Valdés, Carlos ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BICYCLO COMPOUND; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INDOLIZINE DERIVATIVE; QUINOLIZINE DERIVATIVE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; BICYCLO COMPOUNDS; INDICATORS AND REAGENTS; INDOLIZINES; MAGNETIC RESONANCE SPECTROSCOPY; QUINOLIZINES; STEREOISOMERISM;

EID: 0037198756     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0260021     Document Type: Article

References (35)

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4. Some relevant references regarding enantioselective synthesis of indolizidine and quinolizidine alkaloids: (a) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552. (b) Pearson, W. H.; Bergmeier, S. C.; Willians, J. P. J. Org. Chem. 1992, 57, 3977. (c) Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S. Org. Lett. 1999, 1, 107-110. (d) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1999, 64, 3736-3740. (e) Kündig, E. P.; Ratni, H. Org. Lett. 1999, 1, 1997-1999.
5. Some relevant references regarding enantioselective synthesis of indolizidine and quinolizidine alkaloids: (a) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552. (b) Pearson, W. H.; Bergmeier, S. C.; Willians, J. P. J. Org. Chem. 1992, 57, 3977. (c) Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S. Org. Lett. 1999, 1, 107-110. (d) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1999, 64, 3736-3740. (e) Kündig, E. P.; Ratni, H. Org. Lett. 1999, 1, 1997-1999.
6. Some relevant references regarding enantioselective synthesis of indolizidine and quinolizidine alkaloids: (a) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552. (b) Pearson, W. H.; Bergmeier, S. C.; Willians, J. P. J. Org. Chem. 1992, 57, 3977. (c) Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S. Org. Lett. 1999, 1, 107-110. (d) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1999, 64, 3736-3740. (e) Kündig, E. P.; Ratni, H. Org. Lett. 1999, 1, 1997-1999.
7. Some relevant references regarding enantioselective synthesis of indolizidine and quinolizidine alkaloids: (a) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552. (b) Pearson, W. H.; Bergmeier, S. C.; Willians, J. P. J. Org. Chem. 1992, 57, 3977. (c) Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S. Org. Lett. 1999, 1, 107-110. (d) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1999, 64, 3736-3740. (e) Kündig, E. P.; Ratni, H. Org. Lett. 1999, 1, 1997-1999.
8. Some relevant references regarding enantioselective synthesis of indolizidine and quinolizidine alkaloids: (a) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543-4552. (b) Pearson, W. H.; Bergmeier, S. C.; Willians, J. P. J. Org. Chem. 1992, 57, 3977. (c) Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S. Org. Lett. 1999, 1, 107-110. (d) Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1999, 64, 3736-3740. (e) Kündig, E. P.; Ratni, H. Org. Lett. 1999, 1, 1997-1999.
9. (a) Barluenga, J.; Aznar F.; Valdés, C.; Cabal, M. P.; J. Org. Chem. 1993, 58, 3391-3396.
10. (b) Barluenga, J.; Aznar, F.; Valdés, C.; Martín, A.; García-Granda, S.; Martín, E. J. Am. Chem. Soc. 1993, 115, 4403-4404.
11. (c) Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C.; Fernández, M.; Cabal, M. P.; Trujillo, J. Chem. Eur. J. 1996, 2, 805-811.
12. (d) Barluenga, J.; Aznar, F.; Valdés, C.; Ribas, C. J. Org. Chem. 1998, 63, 3918-3924.
13. For reviews, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987, Chapter 2. (b) Waldmann, H. Synthesis 1994, 535. (c) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. (d) Waldmann, H. Synlett 1995, 133. (e) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 190. (f) Weinreb, S. M.; Top. Curr. Chem. 1997, 190, 131. (g) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (h) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
14. For reviews, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987, Chapter 2. (b) Waldmann, H. Synthesis 1994, 535. (c) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. (d) Waldmann, H. Synlett 1995, 133. (e) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 190. (f) Weinreb, S. M.; Top. Curr. Chem. 1997, 190, 131. (g) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (h) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
15. For reviews, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987, Chapter 2. (b) Waldmann, H. Synthesis 1994, 535. (c) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. (d) Waldmann, H. Synlett 1995, 133. (e) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 190. (f) Weinreb, S. M.; Top. Curr. Chem. 1997, 190, 131. (g) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (h) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
16. For reviews, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987, Chapter 2. (b) Waldmann, H. Synthesis 1994, 535. (c) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. (d) Waldmann, H. Synlett 1995, 133. (e) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 190. (f) Weinreb, S. M.; Top. Curr. Chem. 1997, 190, 131. (g) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (h) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
17. For reviews, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987, Chapter 2. (b) Waldmann, H. Synthesis 1994, 535. (c) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. (d) Waldmann, H. Synlett 1995, 133. (e) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 190. (f) Weinreb, S. M.; Top. Curr. Chem. 1997, 190, 131. (g) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (h) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
18. For reviews, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987, Chapter 2. (b) Waldmann, H. Synthesis 1994, 535. (c) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. (d) Waldmann, H. Synlett 1995, 133. (e) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 190. (f) Weinreb, S. M.; Top. Curr. Chem. 1997, 190, 131. (g) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (h) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
19. For reviews, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987, Chapter 2. (b) Waldmann, H. Synthesis 1994, 535. (c) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. (d) Waldmann, H. Synlett 1995, 133. (e) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 190. (f) Weinreb, S. M.; Top. Curr. Chem. 1997, 190, 131. (g) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (h) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
20. For reviews, see: (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987, Chapter 2. (b) Waldmann, H. Synthesis 1994, 535. (c) Weinreb, S. M. Acc. Chem. Res. 1985, 18, 16. (d) Waldmann, H. Synlett 1995, 133. (e) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 190. (f) Weinreb, S. M.; Top. Curr. Chem. 1997, 190, 131. (g) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (h) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
21. Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C. J. Org. Chem. 1999, 64, 3736-3740.
22. Recent reviews concerning solid-phase organic synthesis: (a) Dörwald, F. Z. Organic Chemistry in Solid Phase; Wiley - VCH: Weinheim, Germany, 2000. (b) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies: Wiley: New York, 2000. (c) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (d) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157. (f) Wendeborn, S.; de Mesmaeker, A.; Wolfgang, K.; Brill, D.; Berteina, S. Acc. Chem. Res. 2000, 32, 215-224.
23. Recent reviews concerning solid-phase organic synthesis: (a) Dörwald, F. Z. Organic Chemistry in Solid Phase; Wiley - VCH: Weinheim, Germany, 2000. (b) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies: Wiley: New York, 2000. (c) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (d) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157. (f) Wendeborn, S.; de Mesmaeker, A.; Wolfgang, K.; Brill, D.; Berteina, S. Acc. Chem. Res. 2000, 32, 215-224.
24. Recent reviews concerning solid-phase organic synthesis: (a) Dörwald, F. Z. Organic Chemistry in Solid Phase; Wiley - VCH: Weinheim, Germany, 2000. (b) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies: Wiley: New York, 2000. (c) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (d) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157. (f) Wendeborn, S.; de Mesmaeker, A.; Wolfgang, K.; Brill, D.; Berteina, S. Acc. Chem. Res. 2000, 32, 215-224.
25. Recent reviews concerning solid-phase organic synthesis: (a) Dörwald, F. Z. Organic Chemistry in Solid Phase; Wiley - VCH: Weinheim, Germany, 2000. (b) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies: Wiley: New York, 2000. (c) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (d) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157. (f) Wendeborn, S.; de Mesmaeker, A.; Wolfgang, K.; Brill, D.; Berteina, S. Acc. Chem. Res. 2000, 32, 215-224.
26. Recent reviews concerning solid-phase organic synthesis: (a) Dörwald, F. Z. Organic Chemistry in Solid Phase; Wiley - VCH: Weinheim, Germany, 2000. (b) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies: Wiley: New York, 2000. (c) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (d) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157. (f) Wendeborn, S.; de Mesmaeker, A.; Wolfgang, K.; Brill, D.; Berteina, S. Acc. Chem. Res. 2000, 32, 215-224.
27. Recent reviews concerning solid-phase organic synthesis: (a) Dörwald, F. Z. Organic Chemistry in Solid Phase; Wiley - VCH: Weinheim, Germany, 2000. (b) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies: Wiley: New York, 2000. (c) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (d) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157. (f) Wendeborn, S.; de Mesmaeker, A.; Wolfgang, K.; Brill, D.; Berteina, S. Acc. Chem. Res. 2000, 32, 215-224.
28. For a recent example of the synthesis of bicyclic alkaloids making use of the RCM reaction, see: Liras, S.; Allen, M. P.; Blake, J. F. Org. Lett. 2001, 3, 3483-3486.
29. This process had not been observed for the analogous N-H-substituted piperidones but was known for carbocycles with the same arrangement of ketone and hydroxy functionalities. Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C. J. Org. Chem. 1998, 63, 10052.
30. The low yield of the reaction sequence is motivated by several reasons, mainly, partial deprotection of the silyl ether and the difficulty of purification of the final compound from the reaction crude.
31. 1H NMR spectra and NOESY experiments.
32. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
33. It is worth noting that very few examples have been reported to date of the participation of α,β-unsaturated esters ring-closing metathesis. Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. Moreove very scarce examples have described the participation of tertiary amines in ring-closing metathesis promoted by Grubbs catalysts: Fu, G. C.; Nguyen S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857. Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866-867.
34. It is worth noting that very few examples have been reported to date of the participation of α,β-unsaturated esters ring-closing metathesis. Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. Moreove very scarce examples have described the participation of tertiary amines in ring-closing metathesis promoted by Grubbs catalysts: Fu, G. C.; Nguyen S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857. Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866-867.
35. It is worth noting that very few examples have been reported to date of the participation of α,β-unsaturated esters ring-closing metathesis. Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550. Moreove very scarce examples have described the participation of tertiary amines in ring-closing metathesis promoted by Grubbs catalysts: Fu, G. C.; Nguyen S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857. Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866-867.