5,15-Disubstituted porphyrins are valuable compounds in bioorganic and materials chemistry. A new rational synthesis has been developed that employs condensation of a dipyrromethane + a 1,9-disubstituted dipyrromethane derivative affording the zinc porphyrin. Several C1 synthons have been investigated at the 1,9-positions of the dipyrromethane. The synthesis is compatible with diverse meso-substituents (e.g., H, alkyl, aryl, ester, acetal) and enables rapid synthesis of trans-AB-, A2-, and A-porphyrins without detectable scrambling. The synthesis of >50 zinc porphyrins has been surveyed.
Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster