A new route for installing the isocyclic ring on chlorins yielding 13 1-oxophorbines.
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.
Laha
Joydev K
JK
Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
Muthiah
Chinnasamy
C
Taniguchi
Masahiko
M
Lindsey
Jonathan S
JS
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
D006571:Heterocyclic Compounds; D011166:Porphyrins; C006969:chlorin