英格拉霉素右部片断的合成

Synthesis of Right Segment of Ingramycin

英格拉霉素右部片断含有挑战性的手性叔醇结构.以本实验室发展的[2,3]-Meisenheimer重排为关键反应,以D-丝氨酸为起始原料,经Wittig反应、[2,3]-Meisenheimer重排、NaBH4选择性还原酯基等15步反应,合成了英格拉霉素右部片断,总收率为28%,ee值为90%.

The right segment of ingramycin contains a synthesis-challenging chiral tertiary alcohol structural motif. Based on methodology developed on our laboratory to construct chiral tertiary alcohols via[2,3]-Meisenheimer rearrangement, the synthesis of right segment of ingramycin was successfully achieved over fifteen steps via successive Wittig reaction,[2,3]-Meisenheimer rearrangement, selective ester group reduction with NaBH4, and etc. The total yield was 28% and ee value was 90%.