Synthesis of methyl C132-alkylated pheophorbides a/a′ and their stereochemical characterization

Add time:09/07/2019    Source:sciencedirect.com

C132-Alkylations of a 9:1 epimeric mixture of methyl pheophorbide a/a′, derived from naturally occurring chlorophyll a, were examined by using primary, secondary, and tertiary alkyl iodides. The sterically undemanding C132-alkylation of the methyl pheophorbide epimers successfully afforded their major (132R)- and minor (132S)-adducts, while the isopropylation primarily gave the (132S)-product and no desired adducts were obtained for tert-butyl and neopentyl substituents. The C132-alkylated epimers were separated by reverse phase-HPLC techniques and their stereochemistry was characterized by 1D/2D NMR spectroscopy.

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