Incorporation of an Amino Function in a (1S,2S,3R)-3-Hydroxy-2-methoxy-1-cyclohexane Carboxylic Acid

Abstract

(1S,2S,3R)-3-Hydroxy-2-methoxy-1-cyclohexanecarboxylic acid was synthesized for the construction of an amino acid to be used in a constrained ring didemnin B analog ( 2 ). The amine functionality was introduced into the cyclohexane ring by reductive amination using sodium triacetoxyborohydride or by oxime formation followed by reduction.