Highly efficient synthesis of novel methyl 13(2)-methylene mesopyropheophorbide a and its stereoselective Michael addition reaction

Org Biomol Chem. 2015 Feb 21;13(7):1992-5. doi: 10.1039/c4ob02491e.

Abstract

Treatment of methyl mesopyropheophorbide a with formaldehyde under basic conditions gave a novel 13(2)-methylene derivative in 85% yield; under acidic conditions, the corresponding 20-hydroxymethyl derivative was obtained in 65% yield. The high reactivity of the enone structural motif existed in the former product provides a unique way to construct some novel chlorophyll a derivatives for various applications. Stereoselective Michael reaction of this compound is studied and discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Formaldehyde / chemistry*
  • Molecular Conformation
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry
  • Stereoisomerism

Substances

  • Porphyrins
  • Formaldehyde