Regioselective syntheses of 2,3,4-tribromopyrrole and 2,3,5-tribromopyrrole.
2,3,4-Tribromopyrrole (1) and 2,3,5-tribromopyrrole (2) were each synthesized from pyrrole. Spectral data and antifeedant effects for synthetic 1 and the antipredatory chemical defense compound of the marine hemichordate Saccoglossus kowalevskii were in agreement, confirming the structure of the deterrent natural product as 1. Spectral data for 2 differed from synthetic and natural 1.
John
Ejae A
EA
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA.
Pollet
Pamela
P
Gelbaum
Leslie
L
Kubanek
Julia
J
D000818:Animals; D002816:Chordata, Nonvertebrate / Q000737:chemistry*; D005247:Feeding Behavior / Q000187:drug effects*; D023781:Fundulidae / Q000502:physiology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011235:Predatory Behavior; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C495018:2,3,4-tribromopyrrole; C495019:2,3,5-tribromopyrrole; D011758:Pyrroles