The synthesis of dolaisoleuine as its ieri-butyl ester (Dil-OBut), a β-methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between. N-(benzyloxycarbonyl)-N-methyl-(S,S)-isoleucinaland ieri-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.
ASJC Scopus subject areas
- Organic Chemistry