A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicilin
A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicilin
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DOI：
10.1021/ol991214s
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发表时间：
2000-01-27
期刊：
影响因子：
5.2
通讯作者：
Ley, SV
中科院分区：
文献类型：
--
作者：
Dixon, DJ;Foster, AC;Ley, SV
本文描述了一种短而高效的合成多羟基内酯(+)-aspicilin 1的方法，采用立体选择性高氯酸锂催化的烯丙基三丁基锡加成至等温处理的3（源自（R‘，R’，R，S）丁烷二缩醛保护的丁烷四醇2）的甲醛。末端基团处理和磷酸酯4的Masamune-Roush烯化，再通过合环复合进行大环化，得到部分加氢和整体脱保护后的天然产物。
[GRAPHICS]A short and efficient synthesis of the polyhydroxylated macrolactone (+)-aspicilin 1 using a stereoselective lithium perchlorate mediated addition of allyltributyltin to the equatorially disposed carboxaldehyde of 3 (derived from (R',R',R,S) butane diacetal protected butane tetrol 2) as the key step is described. Terminal group manipulation and Masamune-Roush olefination using phosphonate ester 4 followed by macrocyclization via ring closing metathesis afforded the natural product after partial hydrogenation and global deprotection.