The amide tail synthesis (scheme 7) was based on an asymmetric Aldol reaction. The starting compound is the commercially available Benzyloxyacetic acid 53 which was converted to the thio ester 55 (Ethanethiol) through the acid chloride 54 (thionyl chloride, pyridine). This formed the silyl enol ether 55 (n-butyllithium, trimethylsilyl chloride, Diisopropylamine) which reacted with chiral amine catalyst 58, tin triflate and nBu(OAc) in a Mukaiyama aldol addition with benzaldehyde to alcohol 59 with 99% anti selectivity and 96% ee. The next step converting the alcohol group to an amine in 60 was a Mitsunobu reaction (hydrogen azide, diethyl azodicarboxylate, triphenylphosphine with azide reduction to amine by PhP). The amine group was benzoylated with benzoyl chloride (61) and hydrolysis removes the thioether group in 62.