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Pteridines. Part LXXXV . Chemical synthesis of deoxysepiapterin and 6‐acylpteridines by acyl radical substitution reactions
Author(s) -
Baur Ralph,
Sugimoto Takashi,
Pfleiderer Wolfgang
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710305
Subject(s) - chemistry , pteridine , acylation , homolysis , nucleophilic substitution , bond cleavage , nucleophile , substitution reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis , radical , enzyme
A new synthesis of deoxysepiapterin ( 2 ), one of the two yellow eye pigments of the Drosophila mutant sepia , is described. The synthetic approach makes use of a homolytic nucleophilic acylation of 7‐(alkylthio)pteridine derivatives ( 11, 13, 15, 18, 20 ) leading to the corresponding 6‐acyl derivatives ( 21–27 ). Desulfurizations have been achieved for the first time in the pteridine series using Raney ‐Co, Raney ‐Cu, or CuAl alloy in alkaline medium. Besides cleavage of the C(7)S bond, further reductions of the CO group at C(6) and the C(7)N(8) bond are detected as side reactions leading to 6‐(1‐hydroxyalkyl) ( 34, 35, 42, 43 ) and 6‐acyl‐7,8‐dihydro derivatives ( 2, 36, 37 ), respectively, The newly synthesized compounds have been characterized by elemental analysis, p K determination, UV and 1 H‐NMR spectra.