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Synthesis 2005(14): 2284-2286
DOI: 10.1055/s-2005-869995
DOI: 10.1055/s-2005-869995
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New YorkA Facile Synthesis of Rubrolide E [1]
Further Information
Received
4 March 2005
Publication Date:
13 July 2005 (online)
Publication History
Publication Date:
13 July 2005 (online)

Abstract
A simple and efficient synthesis of rubrolide E (1e) has been demonstrated via Meerwein coupling reaction of para-anisyldiazonium chloride with N-phenylmaleimide (2), regioselective reduction of para-anisylmaleic anhydride (4), Knoevenagel condensation of butyrolactone 5 with para-anisaldehyde and demethylation pathway.
Key words
N-phenylmaleimide - Meerwein coupling - regioselective reduction - Knoevenagel condensation - rubrolide E - total synthesis
NCL Communication No. 6680.
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References
NCL Communication No. 6680.