American Chemical Society
jo0608265_si_001.cif (27.8 kB)

A New Route for Installing the Isocyclic Ring on Chlorins Yielding 131-Oxophorbines

Download (27.8 kB)
posted on 2006-09-01, 00:00 authored by Joydev K. Laha, Chinnasamy Muthiah, Masahiko Taniguchi, Jonathan S. Lindsey
A new route to 131-oxophorbines, the parent macrocycle of chlorophylls, begins with the synthesis of a 13-bromochlorin. Pd-mediated coupling of the latter with tributyl(1-ethoxyvinyl)tin and subsequent acidic hydrolysis afforded the 13-acetylchlorin (1). Treatment of 1 with NBS afforded the 15-bromo analogue in 70% yield. Pd-mediated α-arylation closed the isocyclic ring to give the 131-oxophorbine (2) in 85% yield. Facile access to 131-oxophorbines should enable a variety of spectroscopic studies and diverse applications.