A Single-Flask Synthesis of Morita–Baylis–Hillman Adducts from Ethoxyacetylene and Carbonyl Compounds: Synthesis of Subamolides D and E
A Single-Flask Synthesis of Morita–Baylis–Hillman Adducts from Ethoxyacetylene and Carbonyl Compounds: Synthesis of Subamolides D and E
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由乙氧基乙炔和羰基化合物单瓶合成 Morita-Baylis-Hillman 加合物：Subamolides D 和 E 的合成
DOI：
10.1021/acs.orglett.6b01772
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发表时间：
2016
期刊：
影响因子：
5.2
通讯作者：
Minehan, Thomas G.
中科院分区：
文献类型：
--
作者：
Ng, Kevin;Minehan, Thomas G.
乙氧基乙炔基锂与醛和/或酮(2和4)以及BF3·OET2相继反应，得到β-羟基烯酸酯5，总收率很好到很好。类似地，1(M=Li)和二羰基化合物6(X=O)或酮/醛缩醛(X=OMe)的组合，然后添加Lewis酸，得到五元、六元和七元羟基环烯羧酸酯。该方法在α-亚烷基内酯天然产物亚氨基内酯D和E的合成中得到了应用。
Sequential treatment of (ethoxyethynyl)lithium with aldehydes and/or ketones (2and4) and BF3·OEt2gives rise to β-hydroxyenoates5in good to excellent overall yields. Similarly, the combination of1(M = Li) and dicarbonyl compounds6(X = O) or keto/aldehyde acetals (X = OMe) followed by the addition of a Lewis acid leads to five-, six-, and seven-membered hydroxycycloalkene carboxyates. The utility of this method is demonstrated in the synthesis of the α-alkylidene lactone natural products subamolide D and E.