6277-13-0Relevant academic research and scientific papers
Efficient synthesis of an A-B-C-tricycle fragment for a structural model of tolyporphin
Hu, Bing C.,Zhou, Wei Y.,Liu, Zu L.,Cai, Chao J.,Xu, Shi C.
experimental part, p. 89 - 100 (2010/11/18)
An efficient stereocontrolled synthesis of an A-B-C-tricycle fragment 7 for a structural model of tolyporphin 3 is described. All the rings were prepared from readily available starting materials. One of the two key steps is a selective ring-opening reaction of the lactone cycle in bicyclolactam-lactone 17 to cyanopyrrolidone 18, which introduces the chirality into synthetic compounds. The other key step is the combination of A ring with B-C-bicycle via a two-time Eschenmoser sulfide contraction. A-B-C-tricycle fragment 7 allows a new approach toward tolypophin compounds and other uroporphinoids.
Carbon-5 Regiospecific Synthesis of Deuteroporphyrin IX
Rezzano, Irene,Buldain, Graciela,Frydman, Benjamin
, p. 3059 - 3063 (2007/10/02)
Benzyl 3-(ethoxycarbonyl)-4-methyl-2-pyrrolecarboxylate was formylated with dimethylformamide (DMF)-phosphorous oxychloride, and the 5-formylpyrrole was obtained in 50percent yield.It was reduced with sodium borohydride to the alcohol, which was condensed with benzyl 3-methyl-4-(ethoxycarbonyl)-2-pyrrolecarboxylate to afford dibenzyldipyrrylmethane in good yield.The latter was transformed into its 5,5'-diformyl derivative which when condensed with bis-4-methylpyrryl>methane afforded the 3,8-bis(ethoxycarbonyl)deuteroporphyrin IX dimethyl ester in 40percent yield.Decarboxylation of the latter in hot hydrochloric acid gave deuteroporphyrin IX (isolated as its dimethyl ester) in 50percent yield.
