145696-53-3Relevant academic research and scientific papers
Synthesis of deoxophylloerythroetioporphyrin (DPEP) and three ring homologs by an improved b-bilene methodology
Li, Wei,Lash, Timothy D.
, p. 8571 - 8574 (1998)
Deoxophylloerythroetioporphyrin, an important porphyrin molecular fossil from oil shales and petroleum, and three homologs with six-, seven- or eight- membered exocyclic rings have been prepared by a one pot cyclization of b- bilenes with TFA-trimethyl or
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.
The chemistry of pyrrolic compounds. LXXI synthesis of the ring c and the ring D demethyl analogues of deoxophylloerythroetioporphyrin (dpep)
Clezy, Peter S.,Salek, Abdoreza
, p. 265 - 272 (2007/10/03)
The demethyl analogues (1d,e) of dpep have been prepared by utilizing in each case an oxidative cyclization of an intermediate biladiene-ac to assemble the porphyrin macrocycle.
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
