A Single-Flask Synthesis of Morita–Baylis–Hillman Adducts from Ethoxyacetylene and Carbonyl Compounds: Synthesis of Subamolides D and E
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  • 作者:Kevin Ng ; Thomas G. Minehan
  • 刊名:Organic Letters
  • 出版年:2016
  • 出版时间:August 19, 2016
  • 年:2016
  • 卷:18
  • 期:16
  • 页码:4028-4031
  • 全文大小:348K
  • 年卷期:0
  • ISSN:1523-7052
文摘
Sequential treatment of (ethoxyethynyl)lithium with aldehydes and/or ketones (2 and 4) and BF3·OEt2 gives rise to β-hydroxyenoates 5 in good to excellent overall yields. Similarly, the combination of 1 (M = Li) and dicarbonyl compounds 6 (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.

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