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

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

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, intramole...

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Veröffentlicht in:Helvetica chimica acta 2012-05, Vol.95 (5), p.852-857
Hauptverfasser: Tale, Nilesh P., Shelke, Amol V., Tiwari, Girdharilal B., Thorat, Prerana B., Karade, Nandkishor N.
Format: Artikel
Sprache:eng
Schlagworte:
Knoevenagel condensation
Koser reagent
Rubrolides C and E
Wittig reaction
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Zusammenfassung: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.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201100351