83113-34-2Relevant academic research and scientific papers
Metal-catalyzed oxidative cyclizations of a,c-biladiene salts bearing 1- and/or 19-arylmethyl substituents: Macrocyclic products and their chemistry
Lin, Jack J.,Gerzevske, Kevin R.,Liddell, Paul A.,Senge, Mathias O.,Olmstead, Marilyn M.,Khoury, Richard G.,Weeth, Brent E.,Tsao, Stephanie A.,Smith, Kevin M.
, p. 4266 - 4276 (2007/10/03)
Several 1-mono- and 1,19-bis(p-arylmethyl)-a,c-biladiene salts were prepared and subjected to either copper(II)- or chromium(III)-assisted oxidative cyclization to yield numerous products in which the 1- or 19- substituent is adapted, eliminated, or rearranged to other points on the tetrapyrrole. For example, cyclization using copper(II) acetate of 19- ((ethoxycarbonyl)methyl)-2,3,7,8,12,13,17,-18-octamethyl-19-(p-tolylmethyl)- a,c-biladiene dihydrobromide (25) yielded the copper(II) 20- ((ethoxycarbonyl)methyl)-1-(p-tolylmethyl)-2,3,7,8,12,13,17,18-octamethyl- 1,20-dihydroporphyrin (42), copper(II) 20-(ethoxycarbonyl)-3-methylidene- 2,3,7,8,12,13,17,18-octamethyl-2-(p-tolylmethyl)-chlorin (44), copper(II) 20- (ethoxycarbonyl)-2-methylidene-2,3,7,8,12,13,17,18-octamethyl-3-(p- tolylmethyl)chlorin (45), and three porphyrins: copper(II) 20- (ethoxycarbonyl)-2,3,7,8,12,13,17,18-octamethylporphyrin (3), copper(II) 2,3,7,8,12,13,17,18-octamethyl-20-p-tolylporphyrin (50), and copper(II) 20- (ethoxycarbonyl)-2,3,7,8,12,13,17,18-octamethyl-5-(p-tolylmethyl)porphyrin (47). Formation of porphyrin 47 and the intermediate chlorins 44 and 45 suggests the stepwise migration of the arylmethyl group from the 1-position in compound. 42. The isolation of products from cyclization reactions of various 1,19-arylmethyl-substituted a,c-biladiene salts provides further insight into the mechanisms of metal-assisted oxidative cyclization of a,c- biladiene salts to give cyclic tetrapyrroles. Macrocyclizations of a,c- biladienes such as 25 using chromium(III) afford good yields of the metal- free 1-substituted compounds such as 43.
THE TOTAL SYNTHESIS OF BILIVERDINS OF BIOLOGICAL INTEREST
Awruch, Josefina,Frydman, Benjamin
, p. 4137 - 4146 (2007/10/02)
The total synthesis of eight biliverdin isomers was achieved by oxidation of the corresponding 1,19-di-t-butyloxycarbonyl-b-bilenes.One of the biliverdin isomers is mesobiliverdin IXα - a dipropionate bilitriene -, one is a diacetate bilitriene, three iso
Reactions on solid supports part II: a convenient method for synthesis of pyrromethanes using a montmorillonite clay as catalyst
Jackson, Anthony H.,Pandey, Ravindra K.,Nagaraja Rao,Roberts, Edward
, p. 793 - 796 (2007/10/02)
α-Acetoxymethylpyrroles couple with α-free pyrroles in presence of Montmorillonite clay to form unsymmetrical pyrromethanes in excellent yields. Symmetrical pyrromethanes were also prepared in a similar manner by clay catalysed self-condensation of α-acet
Synthetic Approaches to Versatile Hemoprotein Model Compounds Built from Porphyrins and Peptides
Jackson, Anthony H.,Kenner, George W.,Smith, Kevin M.,Suckling, Colin J.
, p. 1441 - 1448 (2007/10/02)
Several strategies for the preparation of mono- and bi-functional porphyrins (amino and carboxylate) to which oligopeptides can be attached have been investigated.A porphyrinyl amino-acid derivative has been synthesised by coupling a porphyrin monopropion
