Previous Article in event
Next Article in event
Synthesis of Enantiopure Methyl (1S,2S,3R,4S,5R)-2-Amino-3,4,5-trihydroxycyclopentanecarboxylate
Published: 29 November 2008 by MDPI in The 12th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
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.