Cong Xin, Yao Zhu-Jun
State Key Laboratory of Bioorganic and Natural Product Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
J Org Chem. 2006 Jul 7;71(14):5365-8. doi: 10.1021/jo060633h.
(3R,4R,5S)-4-Acetylamino-5-amino-3-hydroxy-cyclohex-1-ene-carboxylic acid ethyl ester, a functionalized cyclohexene skeleton of GS4104, was diastereoselectively synthesized. A major advantage of this synthesis is the use of readily available L-serine to replace frequently used (-)-shikimic acid or (-)-quinic acid as the starting material. Ring-closing metathesis and diastereoselective Grignard reactions successfully served as the key steps. Absolute configurations of the key intermediates were confirmed by corresponding two-dimensional NMR studies.
(3R,4R,5S)-4-乙酰氨基-5-氨基-3-羟基环己-1-烯-羧酸乙酯，GS4104的一种官能化环己烯骨架，被非对映选择性合成。这种合成方法的一个主要优点是使用容易获得的L-丝氨酸替代常用的(-)-莽草酸或(-)-奎尼酸作为起始原料。关环复分解反应和非对映选择性格氏反应成功地作为关键步骤。关键中间体的绝对构型通过相应的二维核磁共振研究得以确认。
