4.3 Article

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

Journal

HELVETICA CHIMICA ACTA
Volume 95, Issue 5, Pages 852-857

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.201100351

Keywords

Rubrolides C and E; Koser reagent; Wittig reaction; Knoevenagel condensation

Funding

  1. Department of Science and Technology, New Delhi, India [SR/S1/OC-72/2009]

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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 a-tosyloxylation of the aryl methyl ketone, intramolecular Wittig reaction, Knoevenagel condensation, and demethylation.

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