New Concise and Efficient Synthesis of Rubrolides C and E via Intramolecular Wittig Reaction

NP Tale, AV Shelke, GB Tiwari, PB Thorat…

Index: Tale, Nilesh P.; Shelke, Amol V.; Tiwari, Girdharilal B.; Thorat, Prerana B.; Karade, Nandkishor N. Helvetica Chimica Acta, 2012 , vol. 95, # 5 p. 852 - 857

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Citation Number: 10

Abstract

Abstract A short total synthesis of rubrolides C and E has been achieved in four steps, using readily available 4-methoxyacetophenone, 2-bromoacetic acid, and the appropriate aromatic aldehyde, in 46 and 45% yield, respectively. Key reactions involved are α- tosyloxylation of the aryl methyl ketone, intramolecular Wittig reaction, Knoevenagel condensation, and demethylation.

~91%

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