Synthesis of substituted butenolides by the ring closing metathesis of two electron deficient olefins: a general route to the natural products of paraconic acids class

A variety of allyl acrylates possessing electron-withdrawing groups undergo RCM using the second generation Grubbs’ catalyst in the presence of a Lewis acid resulting in diverse butenolides in high isolated yields. This methodology provides a general route to the natural products of paraconic acids...

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Bibliographic Details
Published in:Tetrahedron letters 2007-03, Vol.48 (11), p.2021-2024
Main Authors: Selvakumar, N., Kalyan Kumar, P., Chandra Shekar Reddy, K., Chandra Chary, B.
Format: Article
Language:English
Subjects:
Baylis–Hillman reaction
Ring closing metathesis
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Summary:A variety of allyl acrylates possessing electron-withdrawing groups undergo RCM using the second generation Grubbs’ catalyst in the presence of a Lewis acid resulting in diverse butenolides in high isolated yields. This methodology provides a general route to the natural products of paraconic acids class, exemplified by a total synthesis of (±)-phaseolinic acid.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.01.053