Acyclic stereocontrolled synthesis of (−)-detoxinine |
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Authors: | Yasufumi Ohfune Hideki Nishio |
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Affiliation: | Suntory Institute for Bioorganic Research Shimamoto-cho, Mishima-gun, Osaka 618, Japan |
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Abstract: | Allylic oxidation of (2S)-N--butoxycarbonyl-2-amino-4-pentenoic acid methyl ester afforded, stereoselectively, a (2S,3R)-2-amino-3-hydroxyl derivative, which was converted to the unusual amino acid (?)-detoxinine a chelation controlled aldol condensation followed by a pyrrolidine ring formation. |
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