Activated carboxylates from the photooxygenation of oxazoles: Application to the synthesis of recifeiolide, curvularin and other macrolides
HH Wasserman, RJ Gambale, MJ Pulwer
Index: Wasserman, Harry H.; Gambale, Ronald J.; Pulwer, Mitchell J. Tetrahedron, 1981 , vol. 37, # 23 p. 4059 - 4067
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Citation Number: 68
Abstract
Oxazoles may be used as masked forms of activated carboxylic acids since they readily form triamides on reaction with singlet oxygen. With 2-alkyl-4, 5-diphenyloxazoles, the triamides formed on photooxygenation undergo selective nucleophilic attack at the acyl carbonyl derived from the 2-oxazole position. Using 2-(ω-hydroxyalkyl)-4, 5-diphenyloxazoles as substrates, the oxidation-acylation sequence may be employed for the synthesis of ...
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