Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin
Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin
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DOI：
10.1021/jo7027695
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发表时间：
2008-03-21
影响因子：
3.6
通讯作者：
Prodger, Jeremy C.
中科院分区：
文献类型：
--
作者：
Hayes, Christopher J.;Sherlock, Alexandra E.;Prodger, Jeremy C.
在omuralide及其C7-差向异构体和（+）-lactacystin的对映选择性全合成中，亚烷基卡宾1，5-CH插入是关键步骤。合成的另一个值得注意的特征是使用一种新的氧化脱保护程序，利用DMDO，用于将后期亚苄基缩醛转化为伯醇和仲苯甲酸酯。
An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.