78812-89-2Relevant academic research and scientific papers
ACTIVATED CARBOXYLATES FROM THE PHOTOOXYGENATION OF OXAZOLES. APPLICATION TO THE SYNTHESIS OF RECIFEIOLIDE AND OTHER MACROCYCLIC LACTONES.
Wasserman, Harry H.,Gambale, Ronald J.,Pulwer, Mitchell J.
, p. 1737 - 1740 (2007/10/02)
The oxazole system may serve as a protecting group for the carboxyl function.The carboxylate is generated under mild conditions of photooxygenation in high yield in the form of the reactive triamide.This reaction has been applied to the synthesis of macrocyclic lactones.
ACTIVATED CARBOXYLATES FROM THE PHOTOOXYGENATION OF OXAZOLES; APPLICATION TO THE SYNTHESIS OF RECIFEIOLIDE, CURVULARIN AND MACROLIDES
Wasserman, Harry H.,Gambale, Ronald J.,Pulwer, Mitchell J.
, p. 4059 - 4067 (2007/10/02)
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-(ο-hydroxyalkyl)-4,5-diphenyloxazoles as subsrates, the oxidation-acylation sequence may be employed for the synthesis of macrolides including (+/-)-recifeiolide and (+/-)-di-O-methylcurvularin.
