Activated carboxylates from the photooxygenation of oxazoles
1981; Elsevier BV; Volume: 37; Issue: 23 Linguagem: Inglês
10.1016/s0040-4020(01)93281-8
ISSN1464-5416
AutoresHarry H. Wasserman, R. J. GAMBALE, Mitchell J. Pulwer,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoOxazoles 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 macrolides including (±)-recifeiolide and (±)-di-0-methylcurvularin.
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