STUDIES ON THE TOTAL SYNTHESIS OF LACTACYSTIN - AN IMPROVED ALDOL COUPLING REACTION AND A BETA-LACTONE INTERMEDIATE IN THIOL ESTER FORMATION
STUDIES ON THE TOTAL SYNTHESIS OF LACTACYSTIN - AN IMPROVED ALDOL COUPLING REACTION AND A BETA-LACTONE INTERMEDIATE IN THIOL ESTER FORMATION
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DOI：
10.1016/s0040-4039(00)61575-7
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发表时间：
1993-10-29
影响因子：
1.8
通讯作者：
KANIA, R
中科院分区：
文献类型：
--
作者：
COREY, EJ;REICHARD, GA;KANIA, R
对最近开发的lactacystin（1）的全合成方法进行了改进，采用（R）-或（S）-2-硅氧基-1，2，2-三苯基丙酸酯衍生的烯醇化锆分别立体专一地合成（6S，7 R）或（6 R，7S）lactacystin。1的合成中硫羟酸酯的形成主要通过β-内酯中间体进行。
The recently developed total synthesis of lactacystin (1) has been improved by using the zirconium enolate derived from (R)- or (S)-2-siloxy-1,2,2-triphenylpropionate which lead stereospecifically to either (6S,7R) or (6R,7S) lactacystin, respectively. The formation of the thiol ester in the synthesis of 1 proceeds mainly via a beta-lactone intermediate.