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Issue 24, 2012
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Synthesis of anti and syn hydroxy-iso-evoninic acids

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Abstract

The first synthesis of hydroxy-iso-evoninic acid (2), a pyridyl diacid found as a macrodilactone bridging ligand in bioactive Celastraceae sesquiterpenoid-based natural products, has been achieved in 9 steps and an overall yield of 26%. The synthesis utilizes a benzilic ester rearrangement (BER) and a late stage benzylic oxidation to give access to all four stereoisomers whose absolute stereochemistry was assigned following chromatographic separation and anomalous dispersion X-ray crystallography.

Graphical abstract: Synthesis of anti and syn hydroxy-iso-evoninic acids

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Article information


Submitted
26 Mar 2012
Accepted
09 May 2012
First published
10 May 2012

Org. Biomol. Chem., 2012,10, 4685-4688
Article type
Communication

Synthesis of anti and syn hydroxy-iso-evoninic acids

S. A. Warren, S. Stokes, C. S. Frampton, A. J. P. White and A. C. Spivey, Org. Biomol. Chem., 2012, 10, 4685
DOI: 10.1039/C2OB25625H

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