Synthesis of Enantiopure Methyl (1S,2S,3R,4S,5R)-2-Amino-3,4,5-trihydroxycyclopentanecarboxylate

Ramón Estévez; Juan Estévez; Fernando Fernándeza

doi:10.3390/ecsoc-12-01200

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Synthesis of Enantiopure Methyl (1S,2S,3R,4S,5R)-2-Amino-3,4,5-trihydroxycyclopentanecarboxylate

Ramón J. Estévez

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Juan C. Estévez

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Fernando Fernándeza

¹ Departamento de Química Orgánica, Universidade de Santiago de Compostela 15782 Santiago de Compostela, SPAIN

Published: 29 November 2008 by MDPI in The 12th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-12-01200

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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Ramón Estévez

Juan Estévez

Fernando Fernándeza