| Popis: |
(S)-4-Benzyl-3-(p-toluenesulfonyl)-2-oxazolidinone (6) was synthesized as a simplified model substrate for the cyclohexenone subunit (2) of scyphostatin (1) starting from L-phenylalanine (3). Transformation of 6 to (S)-N-(l-benzyl-2-hydroxyethyl)hexadecanamide (10) was efficiently achieved to develop a reliable protocol for the construction of the fatty acid-substituted aminopropanol side chain moiety present in 1; the method involves hydrolysis of the cyclic carbamate moiety, N-palmitoylation of the liberated N-Ts-amido function, and removal of the N-Ts protecting group as the crucial steps. |
