56015-18-0Relevant academic research and scientific papers
Porphyrins with exocyclic rings. Part 22: Synthesis of deoxophylloerythroetioporphyrin (DPEP), three ring homologues, and five related nonpolar bacteriopetroporphyrins using a western ring closure and an improved b-bilene methodology
Lash, Timothy D.,Li, Wei,Quizon-Colquitt, Desiree M.
, p. 12324 - 12342 (2008/03/13)
Dipyrrolic intermediates incorporating five-membered carbocyclic rings are easily prepared from cyclopenta[b]pyrroles, and this unit represents the southern half of the DPEP-type geoporphyrins found in organic-rich sediments such as oil shales and petroleum. Related dipyrroles with six-, seven- or eight-membered carbocyclic rings were shown to give b-bilenes when reacted with dipyrrylmethane carbaldehydes under mildly acidic conditions. Following deprotection of the terminal ester groups, cyclization with TFA-CH(OMe)3 gave a series of ring homologues of deoxophylloerythroetioporphyrin (DPEP). The b-bilenes generated from the five-membered ring dipyrroles proved to be rather unstable and had to be used directly without purification. Cyclization gave DPEP contaminated with an etioporphyrin by-product, but these could be separated as the nickel(II) derivatives by flash chromatography. This approach gave superior yields of DPEP compared to previously reported methods. In addition, the methodology could be extended to the synthesis of related petroporphyrins, and a series of five molecular fossils derived from bacteriochlorophylls d were synthesized by this approach.
A new convergent method for porphyrin synthesis based on a '3 + 1' condensation
Boudif, Arezki,Momenteau, Michel
, p. 1235 - 1242 (2007/10/03)
A new methodology based on the '3 + 1' acid-catalytic condensation of tripyrranes and pyrrole-2,5-dicarbaldehyde has been used, for the first time, for the synthesis of two types of porphyrins: vic-dipropionic ester porphyrins 30 and 31 including an analo
Synthesis of a Porphyrin-2,3-diacrylic Acid using a New '3 + 1' Type Procedure
Boudif, Arezki,Momenteau, Michel
, p. 2069 - 2070 (2007/10/02)
A porphyrin with two acrylic acid substituents on the same pyrrole ring was synthesized using a '3 + 1' type procedure; the electronic state of the porphyrin macrocycle was strongly affected by their presence.
CONCERNING THE MECHANISM OF FORMATION OF BILIVERDINS FROM b-BILENES
Awruch, Josefina
, p. 1171 - 1180 (2007/10/02)
The oxidation of 1,19-di-t-butoxycarbonyl-b-bilenes with bromine affords not only a major biliverdin, but also minor biliverdins.Elucidation of their structure revealed that cleavage of the b-bilene chain takes place during the oxidation, followed by dime
Synthetic and Biosynthetic Studies of Porphyrins. Part 7. The Action of Coproporphyrinogen Oxidase on Coproporphyrinogen-IV: Syntheses of Protoporphyrin-XIII, Mesoporphyrin XIII, and Related Tricarboxylic Porphyrins
Al-Hazimi, Hassan M. G.,Jackson, Anthony H.,Knight, David W.,Lash, Timothy D.
, p. 265 - 276 (2007/10/02)
Coproporphyrinogen-IV (2a) is converted by an enzyme system from chicken blood into a tricarboxylic porphyrinogen (2b) and protoporphyrinogen-XIII (2c).The corresponding porphyrins were isolated as their methyl esters (3b) and (3c) and their structures were deduced by mass and n.m.r. spectrometry (including the use of shift reagents).Confirmation of these conclusions was obtained by total synthesis of the new porphyrins by the MacDonald and ac-biladiene routes.The vinyl groups were introduced either via acetoxyethyl side-chains derived from precursor pyrroles, or by reduction and dehydration of acetyl groups inserted into the porphyrins during the final stages of the syntheses.Mesoporphyrin-XIII dimethyl ester (3m) and the ethyl analogue (3n) of the vinyl tripropionate porphyrin (3b) were also synthesized by the MacDonald route.
