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Synlett 1996; 1996(2): 187-188
DOI: 10.1055/s-1996-5350
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A ‘3+1’ Approach to Monofunctionalized Alkyl Porphyrins

J. L. Sessler* , J. W. Genge, A. Urbach, P. Sansom
  • *Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, U.S.A.
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Publication Date:
31 December 2000 (online)

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A new synthesis of a monofunctionalized β-substituted alkyl porphyrin, 2-(methoxycarbonylethyl)-8,12,13,17-tetraethyl-3,7,18-trimethyl porphyrin (1), is described. It involves the use of a novel ‘3+1’ connectivity approach. Specifically, the mono-substituted tripyrrane, 2,5-bis(5-carboxy-4-ethyl-3-methylpyrrol-2-ylmethyl)-3-(methoxycarbonylethyl)-4-methylpyrrole, was condensed with a doubly activated monomeric pyrrole, 3,4-diethyl-2,5-diformylpyrrole. This yielded porphyrin 1 in 35% yield.

porphyrin - tripyrrane - ‘3+1’ - monohook - diformylpyrrole