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Synthesis 1992; 1992(3): 303-308
DOI: 10.1055/s-1992-26097
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Novel Regio- and Stereoselective Synthesis of 6-Substituted Pteridines and Naturally Occurring L-erythro-Biopterin

Shizuaki Murata* , Takashi Sugimoto, Shoji Ogiwara, Kouichi Mogi, Hiroaki Wasada
  • *Department of Chemistry, College of General Education, Nagoya University, Chikusa, Nagoya 464-01 Japan
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Publication Date:
17 September 2002 (online)

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Condensation of 2,4,5-triamino-6-butoxypyrimidine with various 2-formyloxiranes followed by oxidation with iodine affords 2-amino-4-butoxy-6-(1-hydroxyalkyl)pteridines regioselectively. Naturally occurring L-erythro-biopterin is synthesized from (1S,2S,3S)-2-formyl-3-(1-hydroxyethyl) oxirane. The reaction proceeds via 5,6-dihydropteridine, and the mechanism is discussed with the help of molecular orbital calculations.

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