- Chemoselective oxidation of 6-hydroxyalkylpteridine and its application to synthesis of 6-acyl-7,8-dihydropteridine
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Alcohol-selective oxidation of 6-l′-hydroxyalkylpteridines catalyzed by ruthenium (IV), RuO4-, gives 6-acylpteridines in high yields. Partial reduction of the products affords 6-acyl-7,8-dihydropteridine derivatives, such as a lipophilic derivative of sepiapterin, deoxysepiapterin, and sepiapterin-C.
- Landge, Sudhir S.,Kudoh, Kazunari,Yamada, Yuri,Murata, Shizuaki
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p. 911 - 918
(2008/03/13)
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- Pteridines LXXXV. Chemical Synthesis of Deoxysepiapterin and 6-Acylpteridines by Acyl Radical Substitution Reactions
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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 Cu-Al 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-7,8-dihydro derivatives (2, 36, 37), respectively.The newly synthesized compounds have been characterized by chemical analysis, pK determination, UV and 1H-NMR spectra.
- Baur, Ralph,Sugimoto, Takashi,Pfleiderer, Wolfgang
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p. 531 - 543
(2007/10/02)
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- CHEMICAL SYNTHESIS OF DEOXYSEPIAPTERIN
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A chemical synthesis of the yellow eye pigment deoxysepiapterin of Drosophila melanogaster has been achieved from 7-alkylthio pteridines by homolytic nucleophilic acylation at C-6 and subsequent hydrolyses to 6-proprionylpterin derivatives followed by desulfurizations with copper-aluminium alloy.
- Baur, Ralph,Sugimoto, Takashi,Pfleiderer, Wolfgang
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p. 1025 - 1028
(2007/10/02)
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