Journal of the American Chemical Society

Fragmentation reactions of. alpha.-alkoxy hydroperoxides and application to the synthesis of the macrolide (.+-.)-recifeiolide

SL Schreiber

Index: Schreiber, Stuart L. Journal of the American Chemical Society, 1980 , vol. 102, # 19 p. 6163 - 6165

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Citation Number: 92

Abstract

7 of 3 with 30% H202 in AcOH gave the alkoxy hydroperoxide 4 isolated as a mixture of stereoisomers (99% based on 57% conversion). The addition of FeS04 to a solution of 4 in MeOH saturated with CU (OAC)~ resulted in fragmentation to give the lactone recifeiolide (1) in 96% yield. 7 Inspection of the crude NMR data indicated this was a highly regio-and stereoselective process, as no isomeric olefins could be detected. The mechanism ...

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Activated carboxylates from the photooxygenation of oxazoles: Application to the synthesis of recifeiolide, curvularin and other macrolides

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