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Synthesis of Enantiopure Methyl (1S,2S,3R,4S,5R)-2-Amino-3,4,5-trihydroxycyclopentanecarboxylate
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1  Departamento de Química Orgánica, Universidade de Santiago de Compostela 15782 Santiago de Compostela, SPAIN

Abstract: The first total synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on an intramolecular cyclization leading to 2-oxabicyclo[2.2.1]heptane derivatives. Differences in reactivity for this key step were rationallized by using molecular mechanism based calculations.
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