Pteridines. Part LXXXV. Chemical synthesis of deoxysepiapterin and 6-acylpteridines by acyl radical substitution reactions
✍ Scribed by Ralph Baur; Takashi Sugimoto; Wolfgang Pfleiderer
- Publisher
- John Wiley and Sons
- Year
- 1988
- Tongue
- German
- Weight
- 821 KB
- Volume
- 71
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
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-(alky1thio)pteridine derivatives (1 1, 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 Runey-Co, Runey-Cu, or Cu-A1 alloy in alkaline medium. Besides cleavage of the C(7)-S bond, further reductions of the C=O 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,S-dihydro derivatives (2, 36, 37), respectively. The newly synthesized compounds have been characterized by elemental analysis, pK determination, UV and 'H-NMR spectra.