Novel Stereoselective Synthesis of (R)-3-Aminotetradecanoic Acid (Iturinic Acid)

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.

Cite this article as:

Temperini Andrea, Tiecco Marcello, Testaferri Lorenzo and Terlizzi Raffaella, Novel Stereoselective Synthesis of (R)-3-Aminotetradecanoic Acid (Iturinic Acid), Letters in Organic Chemistry 2009; 6 (1) . https://dx.doi.org/10.2174/157017809787003089