Total synthesis of (±)-martinelline

Tetrahedron Letters

Volumn 43, Issue 51, 2002, Pages 9405-9409

  Xia, Chengfeng ^a   Heng, Linshen ^b   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b Daxian Teacher's College   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ENAMINE; IMINE; IMINO ACID; MARTINELLINE; PYRROLOQUINOLINE; QUINOLINE DERIVATIVE; SQUARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DIELS ALDER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

BETULACEAE;

EID: 0037121605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02331-6     Document Type: Article

References (24)

1. Witherup K.M., Ransom R.W., Graham A.C., Bernard A.M., Salvatore M.J., Lumma W.C., Anderson P.S., Pitzenberger S.M., Varga S.L. J. Am. Chem. Soc. 117:1995;6682.
2. By imino-Diels-Alder strategy, see: (a) Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215; (b) Nieuwenhuyzen, M.; Osborne, D.; Stevenson, P. J.; Thompson, N. Tetrahedron Lett. 2001, 42, 6417; (c) Hadden, M.; Nieuwenhuyzen, M.; Potts, D.; Stevenson, P. J.; Thompson, N. Tetrahedron 2001, 57, 5615; (d) Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj, R. P.; Lough, A. J. Chem. Commun. 1999, 651; (e) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362.
3. By imino-Diels-Alder strategy, see: (a) Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215; (b) Nieuwenhuyzen, M.; Osborne, D.; Stevenson, P. J.; Thompson, N. Tetrahedron Lett. 2001, 42, 6417; (c) Hadden, M.; Nieuwenhuyzen, M.; Potts, D.; Stevenson, P. J.; Thompson, N. Tetrahedron 2001, 57, 5615; (d) Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj, R. P.; Lough, A. J. Chem. Commun. 1999, 651; (e) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362.
4. By imino-Diels-Alder strategy, see: (a) Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215; (b) Nieuwenhuyzen, M.; Osborne, D.; Stevenson, P. J.; Thompson, N. Tetrahedron Lett. 2001, 42, 6417; (c) Hadden, M.; Nieuwenhuyzen, M.; Potts, D.; Stevenson, P. J.; Thompson, N. Tetrahedron 2001, 57, 5615; (d) Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj, R. P.; Lough, A. J. Chem. Commun. 1999, 651; (e) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362.
5. By imino-Diels-Alder strategy, see: (a) Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215; (b) Nieuwenhuyzen, M.; Osborne, D.; Stevenson, P. J.; Thompson, N. Tetrahedron Lett. 2001, 42, 6417; (c) Hadden, M.; Nieuwenhuyzen, M.; Potts, D.; Stevenson, P. J.; Thompson, N. Tetrahedron 2001, 57, 5615; (d) Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj, R. P.; Lough, A. J. Chem. Commun. 1999, 651; (e) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362.
6. By imino-Diels-Alder strategy, see: (a) Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215; (b) Nieuwenhuyzen, M.; Osborne, D.; Stevenson, P. J.; Thompson, N. Tetrahedron Lett. 2001, 42, 6417; (c) Hadden, M.; Nieuwenhuyzen, M.; Potts, D.; Stevenson, P. J.; Thompson, N. Tetrahedron 2001, 57, 5615; (d) Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj, R. P.; Lough, A. J. Chem. Commun. 1999, 651; (e) Batey, R. A.; Powell, D. A. Chem. Commun. 2001, 2362.
7. . By intermolecular [3+2] cycloaddition strategy, see: Nyerges M., Fejes I., Toke L. Tetrahedron Lett. 41:2000;7951.
8. . By CuI-catalyzed coupling strategy, see: Ma D., Xia C., Jiang J., Zhang J. Org. Lett. 3:2001;2189.
9. By intramolecular [3+2] cycloaddition strategy, see: (a) Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron Lett. 1999, 40, 3339; (b) Snider, B. B.; O'Hare, S. M. Tetrahedron Lett. 2001, 42, 2455; (c) Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217; (d) Lovely, C. J.; Mahmud, H. Tetrahedron Lett. 1999, 40, 2079; (e) Mahmud, H.; Lovely, C. J.; Dias, H. V. R. Tetrahedron 2001, 57, 4095; (f) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287.
10. By intramolecular [3+2] cycloaddition strategy, see: (a) Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron Lett. 1999, 40, 3339; (b) Snider, B. B.; O'Hare, S. M. Tetrahedron Lett. 2001, 42, 2455; (c) Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217; (d) Lovely, C. J.; Mahmud, H. Tetrahedron Lett. 1999, 40, 2079; (e) Mahmud, H.; Lovely, C. J.; Dias, H. V. R. Tetrahedron 2001, 57, 4095; (f) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287.
11. By intramolecular [3+2] cycloaddition strategy, see: (a) Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron Lett. 1999, 40, 3339; (b) Snider, B. B.; O'Hare, S. M. Tetrahedron Lett. 2001, 42, 2455; (c) Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217; (d) Lovely, C. J.; Mahmud, H. Tetrahedron Lett. 1999, 40, 2079; (e) Mahmud, H.; Lovely, C. J.; Dias, H. V. R. Tetrahedron 2001, 57, 4095; (f) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287.
12. By intramolecular [3+2] cycloaddition strategy, see: (a) Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron Lett. 1999, 40, 3339; (b) Snider, B. B.; O'Hare, S. M. Tetrahedron Lett. 2001, 42, 2455; (c) Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217; (d) Lovely, C. J.; Mahmud, H. Tetrahedron Lett. 1999, 40, 2079; (e) Mahmud, H.; Lovely, C. J.; Dias, H. V. R. Tetrahedron 2001, 57, 4095; (f) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287.
13. By intramolecular [3+2] cycloaddition strategy, see: (a) Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron Lett. 1999, 40, 3339; (b) Snider, B. B.; O'Hare, S. M. Tetrahedron Lett. 2001, 42, 2455; (c) Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217; (d) Lovely, C. J.; Mahmud, H. Tetrahedron Lett. 1999, 40, 2079; (e) Mahmud, H.; Lovely, C. J.; Dias, H. V. R. Tetrahedron 2001, 57, 4095; (f) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287.
14. By intramolecular [3+2] cycloaddition strategy, see: (a) Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron Lett. 1999, 40, 3339; (b) Snider, B. B.; O'Hare, S. M. Tetrahedron Lett. 2001, 42, 2455; (c) Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217; (d) Lovely, C. J.; Mahmud, H. Tetrahedron Lett. 1999, 40, 2079; (e) Mahmud, H.; Lovely, C. J.; Dias, H. V. R. Tetrahedron 2001, 57, 4095; (f) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287.
15. By other strategies, see: (a) Kim, S. S.; Cheon, H. G.; Kang, S. K.; Yum, E. K.; Choi, J. K. Heterocycles 1998, 48, 221; (b) Gurjar, M. K.; Pal, S.; Rao, A. V. R. Heterocycles 1997, 45, 231; (c) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287; (d) Frank, K. E.; Aube, J. J. Org. Chem. 2000, 65, 655. (e) Nieman, J. A.; Ennis, M. D. Org. Lett. 2000, 2, 1395.
16. By other strategies, see: (a) Kim, S. S.; Cheon, H. G.; Kang, S. K.; Yum, E. K.; Choi, J. K. Heterocycles 1998, 48, 221; (b) Gurjar, M. K.; Pal, S.; Rao, A. V. R. Heterocycles 1997, 45, 231; (c) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287; (d) Frank, K. E.; Aube, J. J. Org. Chem. 2000, 65, 655. (e) Nieman, J. A.; Ennis, M. D. Org. Lett. 2000, 2, 1395.
17. By other strategies, see: (a) Kim, S. S.; Cheon, H. G.; Kang, S. K.; Yum, E. K.; Choi, J. K. Heterocycles 1998, 48, 221; (b) Gurjar, M. K.; Pal, S.; Rao, A. V. R. Heterocycles 1997, 45, 231; (c) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287; (d) Frank, K. E.; Aube, J. J. Org. Chem. 2000, 65, 655. (e) Nieman, J. A.; Ennis, M. D. Org. Lett. 2000, 2, 1395.
18. By other strategies, see: (a) Kim, S. S.; Cheon, H. G.; Kang, S. K.; Yum, E. K.; Choi, J. K. Heterocycles 1998, 48, 221; (b) Gurjar, M. K.; Pal, S.; Rao, A. V. R. Heterocycles 1997, 45, 231; (c) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287; (d) Frank, K. E.; Aube, J. J. Org. Chem. 2000, 65, 655. (e) Nieman, J. A.; Ennis, M. D. Org. Lett. 2000, 2, 1395.
19. By other strategies, see: (a) Kim, S. S.; Cheon, H. G.; Kang, S. K.; Yum, E. K.; Choi, J. K. Heterocycles 1998, 48, 221; (b) Gurjar, M. K.; Pal, S.; Rao, A. V. R. Heterocycles 1997, 45, 231; (c) Ho, T. C. T.; Jones, K. Tetrahedron 1997, 53, 8287; (d) Frank, K. E.; Aube, J. J. Org. Chem. 2000, 65, 655. (e) Nieman, J. A.; Ennis, M. D. Org. Lett. 2000, 2, 1395.
20. Typical procedure: A mixture of 4-methoxycarbonylaniline (1 mmol), ethyl glyoxalate (1 mmol) and the enamine 4 (1.05 mmol) in 5 mL of acetonitrile was stirred for 40 min at rt. After squaric acid (0.05 mmol) was added, the solution was stirred for 2 h at rt. The mixture was concentrated and chromatographed to afford 6 and 7.
21. +) 506.2053. Found: 506.2082.
22. Feichtinger K., Sings H.L., Baker T.J., Matthews K., Goodman M. J. Org. Chem. 63:1998;8432.
23. Feichtinger K., Zapf C., Sings H.L., Goodman M. J. Org. Chem. 63:1998;3804.
24. +). Found: 1021.6407.