Efficient syntheses of 2-carbomethoxy-3,4-disubstituted pyrroles by the condensation of vinylogous amides with aminomalonate

Bulletin of the Korean Chemical Society

Volumn 22, Issue 12, 2001, Pages 1403-1406

  Kim, Sanghee ^a   Son, Soonjoo ^a   Kang, Heonjoong ^a  

^a Seoul National University   (South Korea)

Author keywords

Cyclocondensation; Lamellarin; Lukianol; Substituted pyrroles

Indexed keywords

AMIDE; MALONIC ACID DERIVATIVE; PYRROLE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0035924905     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Kang, H.; Fenical, W. J. Org. Chem. 1997, 62, 3254.
2. Rudi, A.; Goldberg, I.; Stein, Z.; Frolow, F.; Benayahu, Y.; Schleyer, M.; Kashman, Y. J. Org. Chem. 1994, 59, 999.
3. Palermo, J. A.; Brasco, M. F. R.; Alicia, M.; Seldes, A. M. Tetrahedron 1996, 52, 2727.
4. Yoshida, W. Y.; Lee, K. K.; Carroll, A. R.; Scheuer, P. J. Helv. Chim. Acta 1992, 75, 1721.
5. Anderson, R. J.; Faulkner, D. J.; Cun-Heng, H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492.
6. Davis, R. H.; Carroll, A. R.; Pierens, G. K.; Quinn, R. J. J. Nat. Prod. 1999, 62, 419, and references therein.
7. Boger, D. L.; Boyce, C. W.; Labroli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54.
8. Boger, D. L.; Soenen, D. R.; Boyce, C. W.; Hedrick, M. P.; Jin, Q. J. Org. Chem. 2000, 65, 2479.
9. Lukianol A and lamellarin O dimethyl ether: Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637.
10. Lamellarin O and Q, lukianol A: Banwell, M. G.; Flynn, B. L.; Hamel, E.; Hockless, D. C. R. Chem. Commun. 1997, 207.
11. Lamellarin, K.; Banwell, M. G.; Flynn, B. L.; Hockless, D. C. R. Chem. Commun. 1997, 2259.
12. Lamellarin D and H: Ishibashi, F.; Miyazaki, Y.; Iwao, M. Tetrahedron 1997, 53, 5951.
13. Lamellarin G trimethyl ether: Heim, A.; Terpin, A.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 155.
14. Stomiamide A nonamethyl ether: Ebel, H.; Terpin, A.; Steglich, W. Tetrahedron Lett. 1998, 39, 9165.
15. Polycitrin A: Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941.
16. Lukianol A: Liu, J.-H.; Yang, Q.-C.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3587.
17. Lukianol A: Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. Tetrahedron 1999, 55, 14515.
18. Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Dwornik, K. A. Tetrahedron 1998, 54, 5075.
19. Kleisphehn, G. G. J. Am. Chem. Soc. 1955, 77, 1546.
20. Paine, J. B. III; Dolphin, D. J. Org. Chem. 1985, 50, 5598.
21. Paine, J. B. III; Brough, J. R.; Buller, K. K.; Erikson, E. E. J. Org. Chem. 1987, 52, 3986.
22. Cho, D. H.; Lee, J. H.; Kim, B. H. J. Org. Chem. 1999, 64, 8048.
23. Cyclocondensation of vinylogous amide with α-aminocarbonyl compounds has been reported. See; Cohnen, E.; Dewald, R. Synthesis 1987, 566.
24. Domínguez, E.; Marigorta, E. M. D.; Olivera, R.; SanMartín, R. Synlett 1995, 955.
25. The rather unstable presumed intermediate (7) could be isolated from the reaction mixture by rapid silica gel column chromatography, then transformed into the pyrrole (4) in boiling acetic acid with a lower overall yield (ca. 25-30%). The full characterization of 7 is not an easy task due to its unstability.
26. Talvitie, A.; Mannila, E.; Kral, A. Acta Chem. Scand. 1996, 50, 1143.