Title: Novel Stereoselective Synthesis of (R)-3-Aminotetradecanoic Acid (Iturinic Acid)
Volume: 6
Issue: 1
Author(s): Andrea Temperini, Marcello Tiecco, Lorenzo Testaferri and Raffaella Terlizzi
Affiliation:
Keywords:
β-amino acids, stereoselective synthesis, natural products, selenium, copper catalysis
Abstract: (R)-3-Aminotetradecanoic acid (iturinic acid) has been synthesized starting from dodecanoyl chloride. This new synthetic approach involved the enantioselective reduction of an ynone to the corresponding propargylic alcohol and then into a protected propargylic amine. The iturinic acid was obtained by the transformation of a (phenylseleno)acetylene intermediate into a carboxylic group followed by N-deprotection.