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New efficient total syntheses of derivatives of protoporphyrin‐IX bearing deuteriated methyl groups
Author(s) -
Smith Kevin M.,
Pandey Ravindra K.
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200543
Subject(s) - chemistry , hydrobromide , dimethylformamide , hemin , chloride , carboxylate , protoporphyrin , medicinal chemistry , stereochemistry , organic chemistry , porphyrin , heme , solvent , enzyme
New total syntheses of hemins which are regioselectively deuteriated in the 1,5 (2), 5 (3) or 8 (4) methyl groups are described. Syntheses of hemins 2 and 3 follow the progression from pyrromethane 12 to t ‐butyl tripyrrene‐carboxylate hydrobromide (17 and 30) and then to a,c ‐biladiene dihydrobromide (19 and 31), but for reasons of economy in use of labeled monopyrroles, the o,c‐biladiene dihydrobromide 40 for hemin 4 is approached in an initially “clockwise” manner by synthesis of a benzyl tripyrrene‐carboxylate hydrobromide 37 from the pyrromethane 5. Cyclization of the a,c ‐biladienes (19, 31, and 40) was accomplished by brief heating in dimethylformamide in the presence of copper(II) chloride.