Regioselective syntheses of 2,3,4-tribromopyrrole and 2,3,5-tribromopyrrole

Ejae A John; Pamela Pollet; Leslie Gelbaum; Julia Kubanek

doi:10.1021/np0498399

Regioselective syntheses of 2,3,4-tribromopyrrole and 2,3,5-tribromopyrrole

J Nat Prod. 2004 Nov;67(11):1929-31. doi: 10.1021/np0498399.

Authors

Ejae A John¹, Pamela Pollet, Leslie Gelbaum, Julia Kubanek

Affiliation

¹ School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA.

PMID: 15568793
DOI: 10.1021/np0498399

Abstract

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Animals
Chordata, Nonvertebrate / chemistry*
Feeding Behavior / drug effects*
Fundulidae / physiology*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Predatory Behavior
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Pyrroles / pharmacology

Substances

2,3,4-tribromopyrrole
2,3,5-tribromopyrrole
Pyrroles