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.