Synthesis of tyrosine derivatives for saframycin MX1 biosynthetic studies
Saframycin MX1 and structural relatives are natural anticancer agents isolated from bacteria and marine invertebrates. For biosynthetic studies and to make a library of modified natural products, a series of tyrosine derivatives were synthesized in a conc
Schmidt, Eric W.,Nelson, James T.,Fillmore, John P.
p. 3921 - 3924
(2007/10/03)
A general approach to L-tyrosine porphyrins
A novel and general approach has been developed to prepare L-tyrosine-containing porphyrins. The key intermediates, 2-tert-butoxycarbonylamino-3-(3-formyl-4-hexyloxy-phenyl)-propionic acid hexyl ester and 2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester, were prepared by the Reimer-Tiemann reaction of Boc-protected L-tyrosine, which was followed by esterification and alkylation of the phenol hydroxide. A number of novel chiral L-tyrosine porphyrins were obtained from the reactions of 2-tert-butoxycarbonylamino-3-(3-formyl-4-alkoxy-phenyl)-propionic acid ester with different dipyrrolylmethanes and the reaction of 5-(4-trifluoromethylphenyl)pyrromethane afforded the highest yield. The tyrosine porphyrins could be readily deprotected to afford the corresponding diacid or diamine derivatives.