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Synthesis 2009(17): 2825-2839
DOI: 10.1055/s-0029-1216924
DOI: 10.1055/s-0029-1216924
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Reactivity of Oxazol-5-(4H)-ones and Their Application toward Natural Product Synthesis
Further Information
Received
27 May 2009
Publication Date:
30 July 2009 (online)
Publication History
Publication Date:
30 July 2009 (online)
Abstract
This work reviews the reactivity of oxazolones and their application in the synthesis of natural products. In particular, the focus is on the development and scope of oxazolone-mediated ene-type reactions, 1,3-dipolar cycloadditions, and a novel Claisen-type rearrangement. The utility of these reactions towards natural product synthesis is described.
Key words
oxazolones - azlactones - ene reaction - Claisen rearrangement - 1,3-dipolar cycloaddition
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References
It should be noted that due to the lability of the oxazolone product and tendency to hydrolyze upon chromatographic purification, the quaternary oxazolones were treated with methanol to afford the ring-opened methyl ester. Reported yields of the reaction are of the purified methyl esters.