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

Andrea      Temperini; Marcello      Tiecco; Lorenzo      Testaferri; Raffaella      Terlizzi

doi:10.2174/157017809787003089

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.

Keywords: β-amino acids, stereoselective synthesis, natural products, selenium, copper catalysis

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Letters in Organic Chemistry

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

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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.

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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