AN EFFICIENT, ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN
AN EFFICIENT, ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN
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DOI：
10.1021/jo00351a008
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发表时间：
1986-01-10
影响因子：
3.6
通讯作者：
LUCHE, MJ
中科院分区：
文献类型：
--
作者：
DENIS, JN;GREENE, AE;LUCHE, MJ
不对称环氧化（76- 80%ee）和高度区域选择性的环氧化物裂解已被用作合成紫杉醇侧链甲基酯（2; ≥ 10）的关键反应。95%ee，23%总产率，来自苯乙炔）。2的反式异构化（分四步）已经实现，并且用（-）-异松樟脑酚（8）、1，2; 3，4-二-O-异亚丙基-D-吡喃半乳糖（9）和赤霉素酸甲酯（10）举例说明。
An asymmetric epoxidation (76-80% ee), and a highly regioselective epoxide cleavage have been used as the key reactions in the synthesis of the taxol side chain methyl ester (2; .gtoreq. 95% ee, 23% overall yield from phenylacetylene). Transesterifications of 2 (in four steps) have been effected and are exemplified with (-)-isopinocamphenol (8), 1,2;3,4-di-O-isopropylidene-D-galactopyranose (9), and methyl gibberellate (10).