A new synthesis of 131-oxophorbines, simple mimics of chlorophyll

ORGN 551

Muthiah Chinnasamy, mchinna@unity.ncsu.edu, Joydev K. Laha, jklaha@unity.ncsu.edu, Masahiko Taniguchi, mttanig@yahoo.com, and Jonathan S. Lindsey, jlindsey@ncsu.edu. Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204
Chlorins bearing a keto-group at the 13-position of the macrocycle (termed 131-oxophorbines) are valuable synthetic targets given their resemblance to chlorophyll. We have developed a new mild route for installation of the isocyclic ring on chlorins, which entails regioselective 15-bromination followed by Pd-mediated α-arylation of the 13-acetyl moiety. The resulting zinc-131-oxophorbine exhibits a redshifted Qy band (643 nm), as expected given the close resemblance to naturally occurring chlorophylls.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006