title: A new route for installing the isocyclic ring on chlorins yielding 13 1-oxophorbines.
abstract: A new route to 13(1)-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 alpha-arylation closed the isocyclic ring to give the 13(1)-oxophorbine (2) in 85% yield. Facile access to 13(1)-oxophorbines should enable a variety of spectroscopic studies and diverse applications.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Joydev K
authors.initials: JK
authors.lastname: Laha
authors.forename: Chinnasamy
authors.initials: C
authors.lastname: Muthiah
authors.forename: Masahiko
authors.initials: M
authors.lastname: Taniguchi
authors.forename: Jonathan S
authors.initials: JS
authors.lastname: Lindsey
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013057:Spectrum Analysis / Q000379:methods
chemical_list: D006571:Heterocyclic Compounds; D011166:Porphyrins; C006969:chlorin