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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

Author(s): Andrea Temperini, Marcello Tiecco, Lorenzo Testaferri and Raffaella Terlizzi

Volume 6, Issue 1, 2009

Page: [22 - 24] Pages: 3

DOI: 10.2174/157017809787003089

Price: $65

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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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