16980-14-6Relevant academic research and scientific papers
Total synthesis of chlorophyll c fossils and related petroporphyrins
Bauder,Ocampo,Callot
, p. 2537 - 2540 (1991)
The total synthesis of a series of petroporphyrins related to chlorophyll c is described. These compounds have in common, fused to the porphyrin macrocycle, a methylcyclopentane ring which was obtained via cyclization of an isopropenyl group.
Peripheral Mercuration of Metalloporphyrins: Novel Syntheses of Deoxophylloerythroetioporphyrin and Deoxophylloerythrin Methyl Ester
Smith, Kevin M.,Langry, Kevin C.,Minnetian, Ohannes M.
, p. 4602 - 4609 (1984)
Zinc(II) porphyrins bearing unsubstituted β positions can be mercurated at the β position and at an adjacent meso position.Palladium / olefin reactions with the dimercurated porphyrins produce products possessing a five-membered isocyclic ring bridging the β and meso positions and resembling that found in chlorophyll derivatives.With use of this methodology, novel syntheses of deoxophylloerythroetioporphyrin (2) and deoxophylloerythrin methyl ester (3), two degradation products of chlorophyll, are described.
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.
Total synthesis of the porphyrin mineral abelsonite and related petroporphyrins with five-membered exocyclic rings
Zhang, Bo,Lash, Timothy D.
, p. 7253 - 7256 (2007/10/03)
A reliable synthesis of porphyrins with five-membered exocyclic rings from b-bilenes has been developed. This methodology has been applied to the first total synthesis of the porphyrin mineral abelsonite, as well as the widespread petroporphyrin deoxophyl
Synthesis of deoxophylloerythroetioporphyrin (DPEP) and three ring homologs by an improved b-bilene methodology
Li, Wei,Lash, Timothy D.
, p. 8571 - 8574 (2007/10/03)
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
A novel and convenient conversion of chlorins to phytoporphyrins during the modification of chlorophyll derivatives
Ma, Lifu,Dolphin, David
, p. 7791 - 7794 (2007/10/02)
Chlorophyll derivatives 2a, 2b, 2c and 3 have been readily converted to their corresponding phytoporphyrins 5a, 5b, 5c in excellent yields using benzoyl chloride in DMF. This method affords a new and efficient route to prepare monovinyl porphyrins which can be used as intermediates for the further preparation of chlorophyll related petroporphyrins and regiochemically pure benzoporphyrin derivatives for use in photodynamic therapy.
The Chemistry of Pyrrolic Compounds. LXVIII. 13'- and 15'-Methyl Analogues of Deoxophylloerythroetioporphyrin (dpep)
Bong, Ivy C. C.,Clezy, Peter S.,Fookes, Christopher J. R.,Prashar, Jognandan K.,Salek, Abdoreza
, p. 1193 - 1206 (2007/10/02)
A new synthesis of the 13'- and 15'-methyl (1a) analogue of dpep is described commencing with the methylation of phylloerythroetioporphyrin (1d) with subsequent reduction of the derived tertiary alcohol.The availability of this synthetic materials has allowed the presence of this petroporphyrin as its nickel complex to be confirmed in the Julia Creek oil shales.The presence of an isomer of this petroporphyrin has been noted in the same deposit, and the structure of this novel fossil porphyrin has been confirmed as the 15'-methyl analogue (1b) of dpep by a synthesis commencing from the 15'-oxoporphyrin (1e).In addition, the 15'- and 13'-methyl analogues of dpep have been synthesized by cyclization of appropriately substituted propenyl- and isopropenyl-porphyrins respectively.The origin of these two petroporphyrins is discussed.
Total synthesis of cyclopentenoporphyrins of sedimentary origin: deoxophylloerythroetioporphyrin, chlorophyll c fossils and related compounds.
Bauder, Claude,Ocampo, Ruben,Callot, Henry J.
, p. 5135 - 5150 (2007/10/02)
This article describes the total synthesis of seven porphyrins, fossils of chlorophyll derivatives, isolated from sedimentary sources and possess five-membered rings fused to the porphyrin nucleus, this additional ring being placed between positions 13,15 or 15,17.This ring was built from vinyl, hydroxyethyl or isopropenyl groups under strong acidic conditions. Key words: sedimentary porphyrins, chlorophyll geochemistry, total synthesis, E-ring formation.
Chemistry of Pyrrolic Compounds. XLVI Benzyl β-Keto Propionate Porphyrins: A New Synthesis of Deoxyophylloerythroaetioporphyrin and Harderoporphyrin
Chaudhry, Irshad A.,Clezy, Peter S.,Mirza, Aminul H.
, p. 1095 - 1104 (2007/10/02)
Porphyrins with benzyl β-keto propionate side chains have been prepared by condensation of the appriopriate porphyrin acid chloride with the magnesium chelate of the enolate form of benzyl hydrogen malonate.Intermediates of this class have been used in th
