A new route for installing the isocyclic ring on chlorins yielding 13 1-oxophorbines

J Org Chem. 2006 Sep 1;71(18):7049-52. doi: 10.1021/jo0608265.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Chemistry, Organic / methods*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Porphyrins / chemistry*
  • Spectrometry, Fluorescence
  • Spectrum Analysis / methods

Substances

  • Heterocyclic Compounds
  • Porphyrins
  • chlorin