英格拉霉素右部片断的合成
收稿日期: 2013-07-06
修回日期: 2013-07-27
网络出版日期: 2013-08-13
基金资助
国家自然科学基金(No. 21372205)资助项目
Synthesis of Right Segment of Ingramycin
Received date: 2013-07-06
Revised date: 2013-07-27
Online published: 2013-08-13
Supported by
Project supported by the National Natural Science Foundation of China (No. 21372205)
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%.
关键词： 英格拉霉素; 手性叔醇; [2,3]-Meisenheimer 重排; Wittig反应; NaBH4选择性酯还原
高凯歌 , 孙默然 , 朱明 , 周航 , 曹其伟 , 杨华 . 英格拉霉素右部片断的合成[J]. 有机化学, 2013 , 33(9) : 1939 -1944 . DOI: 10.6023/cjoc201307011
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%.
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