Studies of macrocycle formation leading to synthetic bacteriochlorins

ORGN 101

Marcin Ptaszek, mptasze@ncsu.edu, Han-Je Kim, kim10@fas.harvard.edu, and Jonathan S. Lindsey, jlindsey@ncsu.edu. Department of Chemistry, North Carolina State University, Dabney Hall Box 8204, Yarborough Drive, Raleigh, NC 27695-8204
A new route to stable, synthetic bacteriochlorins relies on the self-condensation of a dihydrodipyrrin-acetal. We have investigated the self-condensation under diverse acid-catalysis conditions (>20 acids; temperature; solvents; additives; concentration) with substrates bearing a variety of substituents in the pyrrole moiety, with the key objective to increase yields and limit formation of other macrocycles (e.g., the tetradehydrocorrin, not shown). The 3,13-dibromobacteriochlorin was a particular focus given its versatility for building block chemistry.

 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008