Events The 12th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 12th International Electronic Conference on Synthetic Organic Chemistry

Published date

29 Nov, 2008

Citation

Fernando Fernándeza, Juan C. Estévez, Ramón J. Estévez, Synthesis of Enantiopure Methyl (1S,2S,3R,4S,5R)-2-Amino-3,4,5-trihydroxycyclopentanecarboxylate, in Proceedings of The 12th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2008, MDPI: Basel, Switzerland, 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 ¹

Juan C. Estévez ¹

Fernando Fernándeza ¹

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.

Keywords

n/a

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