Enantiospecific synthesis of 3-aza-6,8-dioxa-bicyclo[3.2.1]octane carboxylic acids from erythrose |
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Authors: | Andrea TrabocchiGloria Menchi Massimo RollaFabrizio Machetti Ilaria BucelliAntonio Guarna |
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Affiliation: | Dipartimento di Chimica Organica ‘Ugo Schiff’, Università di Firenze, and Istituto di Chimica dei Composti Organometallici-C.N.R., Polo Scientifico di Sesto Fiorentino, Via della Lastruccia 13, I-50019 Sesto Fiorentino, Firenze, Italy |
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Abstract: | New methodology for the synthesis of enantiopure 3-aza-6,8-dioxa-bicyclo[3.2.1]octane-carboxylic acids belonging to 7-endo-BTAa sub-class of γ/δ amino acids is described. The novelty is the use of 2,3-O-isopropylidene-erythrose instead of meso-tartaric acid derivative, thus allowing us to perform an enantiospecific synthesis. Reductive amination of erythrolactol with aminoacetaldehyde diethylacetal or benzylamine, and subsequent acid cyclisation gave directly the amino alcohol scaffold. Protection of nitrogen as urethane and final alcohol oxidation afforded the Fmoc-, Boc-, and Cbz-amino acids. The new synthetic route was applied to multigram scale, thus resulting in a marked improvement of the synthesis of enantiopure 7-endo-BTG and 7-endo-BTK amino acids. |
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Keywords: | amino acids and derivatives peptide mimetics amination bicyclic heterocyclic compounds |
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