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Synlett 1993; 1993(4): 273-274
DOI: 10.1055/s-1993-22428
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A Novel Efficient Synthesis of 1-Ethoxyvinyl Esters and Their Use in Acylation of Amines and Alcohols: Synthesis of Water-Soluble Oxaunomycin Derivatives

Yasuyuki Kita* , Hiroshi Maeda, Kana Omori, Takayuki Okuno, Yasumitsu Tamura
  • *Faculty of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565, Japan
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Publication Date:
19 March 2002 (online)

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1-Ethoxyvinyl esters (1a-i), prepared by the addition of carboxylic acids to ethoxyacetylene in the presence of a catalytic amount of [RuCl2(p-cymene)]2, react with amines (3a-d) and alcohols (5a-e) to give the corresponding N- and O-acylated compounds (4a-l and 6a-f) in high yields. Application of this method to the synthesis of water-soluble oxaunomycin derivatives (9a,b) is also described.