Polyhydroxylated cyclopentane β-amino acids derived from D-mannose and D-galactose: synthesis and protocol for incorporation into peptides

02 August 2021, Version 3
This content is a preprint and has not undergone peer review at the time of posting.


A stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported. The reaction sequence comprises as key steps a Ring Closing Metathesis of a polysubstituted diene intermediate, followed by the stereoselective aza-Michael functionalization of the resulting cyclopent-1- ene-1-carboxylic acid ester. Examples of synthesis of polysubstituted 2-aminocyclopentanecarboxylic acid derivatives starting from protected D-mannose and D-glucose are presented. A general protocol for the incorporation of these highly functionalized alicyclic β-amino acids into peptides is also reported.


Ring Closing Metathesis
Amino acids
asymmetric synthesis
beta-amino acids


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