A simple synthesis of (R)-3-aminooctanoic acid (D-BAO) from (S)-1-octyn-3-ol

A simple substrate-controlled asymmetric synthesis of (R)-3-aminooctanoic acid (D-BAOA) is described. The present method involves the conversion of commercially available (S)-l-octyn-3-ol into the protected propargylic amine, with complete inversion of configuration, and the successive transformation of the (phenylseleno) acetylene intermediate into the Se-phenyl seleno-carboxylate, which is then easily converted into the carboxylic group. The phthalimido group was eventually removed by treatment with hydrazine hydrate.