Synthesis of (2S,3S,8S,9S)-Adda from D-glucose

Article abstract of DOI:10.1016/0040-4039(96)01217-8

The N-trifluoroacetyl derivative of the novel β-amino acid (2S,3S,8S,9S)-Adda methyl ester 4 has been prepared from the D-glucose derived oxazoline 7. A key step in the construction of 4 was the generation of the E,E decadienoate system via dissolving metal reduction of vicinal bis-mesylate 15.