Model
Digital Document
Publisher
Florida Atlantic University
Description
The ensuing treatise details the routes investigated in the
attempt to synthesize a novel porphyrin related to
deoxophylloerythroetioporphyrin (DPEP), containing a fused
six-membered cycloalkano ring system and a carboxylic acid
chain in its structure. Mesorhodin methyl ester, the
intermediate used throughout this study was obtained from
mesoporphyrin dimethyl ester which in turn, was prepared
from hemin.
Attempts to reduce the keto-function in mesorhodin methyl
ester to the corresponding methylene group in our target
coumpound were based on two methods. The first approach
was application of the Huang-Minlon modification of the
Wolff-Kischner reaction. The second procedure considered
chemical and catalytic hydrogenations as well as
dehydration reactions. Although our proposed pathways were
found to be unsatisfactory, the latter methodology did lead
to unreported intermediates and a new porphyrin with a
fused benzene ring. Their syntheses and spectral properties
are discussed.
attempt to synthesize a novel porphyrin related to
deoxophylloerythroetioporphyrin (DPEP), containing a fused
six-membered cycloalkano ring system and a carboxylic acid
chain in its structure. Mesorhodin methyl ester, the
intermediate used throughout this study was obtained from
mesoporphyrin dimethyl ester which in turn, was prepared
from hemin.
Attempts to reduce the keto-function in mesorhodin methyl
ester to the corresponding methylene group in our target
coumpound were based on two methods. The first approach
was application of the Huang-Minlon modification of the
Wolff-Kischner reaction. The second procedure considered
chemical and catalytic hydrogenations as well as
dehydration reactions. Although our proposed pathways were
found to be unsatisfactory, the latter methodology did lead
to unreported intermediates and a new porphyrin with a
fused benzene ring. Their syntheses and spectral properties
are discussed.
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