Synthesis and identification of two halogenated bipyrroles present in seabird eggs

Chemical Communications

Volumn , Issue 21, 1999, Pages 2195-2196

  Gribble, Gordon W ^a   Blank, David H ^a   Jasinski, Jerry P ^b  

^a Dartmouth College   (United States)

^b KEENE STATE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOHALOGEN DERIVATIVE; PYRROLE DERIVATIVE;

ANIMAL TISSUE; ARTICLE; BIRD; CHEMICAL STRUCTURE; EGG; LIVER; NONHUMAN; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033533947     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906655a     Document Type: Article

References (11)

1. G. W. Gribble, Prog. Chem. Org. Nat. Prod., 1996, 68, 1; G.W. Gribble, Acc. Chem. Res., 1998, 31, 141; G.W. Gribble, Chem. Soc. Rev., 1999, 28, 335.
2. G. W. Gribble, Prog. Chem. Org. Nat. Prod., 1996, 68, 1; G.W. Gribble, Acc. Chem. Res., 1998, 31, 141; G.W. Gribble, Chem. Soc. Rev., 1999, 28, 335.
3. G. W. Gribble, Prog. Chem. Org. Nat. Prod., 1996, 68, 1; G.W. Gribble, Acc. Chem. Res., 1998, 31, 141; G.W. Gribble, Chem. Soc. Rev., 1999, 28, 335.
4. S. A. Tittlemier, M. Simon, W. M. Jarman, J. E. Elliott and R. J. Norstrom, Environ. Sci. Technol., 1999, 33, 26.
5. T. Kauffmann and H. Lexy, Chem. Ber., 1981, 114, 3674.
6. J. Bergman and L. Venemalm, J. Org. Chem., 1992, 57, 2495.
7. H. M. Gilow and D. E. Burton, J. Org. Chem., 1981, 46, 2221, report that pyrrole chlorination with NCS is less selective than is bromination with NBS.
8. S. A. Tittlemier and R. J. Norstrom, personal communication, whom we thank for making these comparisons.
9. R. J. Andersen, M. S. Wolfe and D. J. Faulkner, Mar. Biol., 1974, 27, 281.
10. 3 are 'forced metabolites' and are not considered to be natural products: N. Ezaki, M. Koyama, Y. Kodama, T. Shomura, K. Tashiro, T. Tsuruoka, S. Inouye and S. Sakai, J. Antibiot., 1983, 36, 1431. Similarly, bromonitrins A-C, which also contain chlorine and bromine, are only produced when bromide is added to the culture medium and are not considered natural: M. Ajisaka, K. Kariyone, K. Jomon, H. Yazawa and K. Arima, Agric. Biol. Chem., 1969, 33, 294.
11. 3 are 'forced metabolites' and are not considered to be natural products: N. Ezaki, M. Koyama, Y. Kodama, T. Shomura, K. Tashiro, T. Tsuruoka, S. Inouye and S. Sakai, J. Antibiot., 1983, 36, 1431. Similarly, bromonitrins A-C, which also contain chlorine and bromine, are only produced when bromide is added to the culture medium and are not considered natural: M. Ajisaka, K. Kariyone, K. Jomon, H. Yazawa and K. Arima, Agric. Biol. Chem., 1969, 33, 294.