Stereospecific Synthesis of Azetidine-cis-2,3-dicarboxylic Acid.
نویسندگان
چکیده
منابع مشابه
Stereospecific synthesis of azetidine-cis-2,3-dicarboxylic acid.
Electrocyclic reaction product of 1-(methoxycarbonyl)-1,2-dihydropyridine was stereospecifically converted by RuO(4) oxidation into azetidine-cis-2,3-dicarboxylic acid.
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In the title compound, C(8)H(12)O(4), the two carboxyl groups are on the same side of the cyclohexane ring and the ring adopts a chair conformation. Adjacent mol-ecules related by an inversion centre are linked by pairs of O-H⋯O hydrogen bonds, forming a zigzag chain along [1].
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The four stereoisomers of azetidine-2,3-dicaroxylic acid (L-trans-ADC, L-cis-ADC, D-trans-ADC, and D-cis-ADC) were synthesized in a stereocontrolled fashion following two distinct strategies: one providing the two cis-ADC enantiomers and one giving access to the two trans-ADC enantiomers. The four azetidinic amino acids were characterized in a radioligand binding assay ([(3)H]CGP39653) at nativ...
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Regioselective addition of aryl lithium to commercially available (S)-(+)-propylene oxide provides the corresponding (S)-aryl-2-propanol. The (R)-amphetamine is obtained by conversion of the alcohol to the tosylate followed by azide displacement and hydrogenation. Mitsunobu conversion of the alcohol to the (R)-bromide followed by azide displacement and hydrogenation affords the (S)-amphetamine....
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ژورنال
عنوان ژورنال: Chemical and Pharmaceutical Bulletin
سال: 2003
ISSN: 0009-2363,1347-5223
DOI: 10.1248/cpb.51.96