Synthesis of polycitrin A and 3,4-bis(4-hydroxyphenyl)pyrrole derivatives related to polycitone A

Synthesis

Volumn , Issue 18, 2006, Pages 3043-3047

  Winklhofer, Christian ^a   Terpin, Andreas ^a   Peschko, Christian ^a   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Biomimetic synthesis; Bromination; Marine alkaloids; Polycitones; Polycitrins; Pyrroles

Indexed keywords

BIOMIMETIC SYNTHESIS; BROMINATION; MARINE ALKALOIDS; POLYCITONES; POLYCITRINS; PYRROLES;

AMINES; DERIVATIVES; ESTERS; OXIDATION; POLYCONDENSATION; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

3,4 BIS(4 HYDROXYPHENYL) 2,5 BIS(4 HYDROXYBENZOYL) 1 [2 (4 HYDROXYPHENYL)ETHYL]PYRROLE; 3,4 BIS(4 HYDROXYPHENYL)PYRROLE; 3,4 BIS(4 METHOXYPHENYL) 1 [2 (4 METHOXYPHENYL)ETHYL]PYRROLE 2,5 DICARBOXYLIC ACID; ALKALOID DERIVATIVE; MALEIMIDE; POLYCITONE A; POLYCITRIN A; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CRYSTALLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; EXTRACTION; POLYMERIZATION; PURIFICATION;

EID: 33749534875     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950190     Document Type: Article

References (14)

1. Rudi, A.; Goldberg, I.; Stein, Z.; Frolow, F.; Benayahu, Y.; Schleyer, M.; Kashman, Y. J. Org. Chem. 1994, 59, 999.
2. Rudi, A.; Evan, T.; Aknin, M.; Kashman, Y. J. Nat. Prod. 2000, 63, 832.
3. Loya, S.; Rudi, A.; Kashman, Y.; Hizi, A. Biochem. J. 1999, 344, 85.
4. Terpin, A.; Polborn, K.; Steglich, W. Tetrahedron 1995, 51, 9941.
5. Beccalli, E. M.; Clerici, F.; Marchesini, A. Tetrahedron 2000, 56, 2699.
6. Reviews: (a) Carter, H. Org. React. 1946, 3, 198.
7. (b) Steglich, W. Fortschr. Chem. Forsch. 1969, 12, 77.
8. Banwell, M. G.; Goodwin, T. E.; Ng, S.; Smith, J. A.; Wong, D. J. Eur. J. Org. Chem. 2006, 3043.
9. (a) Weinberg, N. L.; Brown, E. A. J. Org. Chem. 1966, 31, 4054.
10. (b) Tedjar, F.; Ymmel, S.; Janda, M.; Duchek, P.; Holy, P.; Stibor, I. Collect. Czech. Chem. Commun. 1989, 54, 1299.
11. Ghelfi, F.; Stevens, C. V.; Laureyn, I.; Van Meenen, E.; Rogge, T. M.; De Buyck, L.; Nikitin, K. V.; Grandi, R.; Libertini, E.; Pagnoni, U. M.; Schenetti, L. Tetrahedron 2003, 59, 1147.
12. Syntheses of polycitone A: (a) Kreipl, A. T.; Reid, C.; Steglich, W. Org. Lett. 2002, 4, 3287.
13. (b) Gupton, J. T.; Miller, R. B.; Krumpe, K. E.; Clough, S. C.; Banner, E. J.; Kanters, R. P. F.; Du, K. X.; Keertikar, K. M.; Lauerman, N. E.; Solano, J. M.; Adams, B. R.; Callahan, D. W.; Little, B. A.; Scharf, A. B.; Sikorski, J. A. Tetrahedron 2005, 61, 1845.
14. Niederl, J. B.; Ziering, A. J. Am. Chem. Soc. 1942, 64, 885.