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Issue 9, 2006
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A highly enantioselective total synthesis of (+)-goniodiol

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Abstract

A high-yielding enantioselective total synthesis of the bioactive styryllactone (+)-goniodiol has been realised, starting from readily available (S)-glycidol. A key step is an oxygen-to-carbon rearrangement of a silyl enol ether linked via an anomeric centre, facilitating the rapid and diastereoselective construction of this functionalised system.

Graphical abstract: A highly enantioselective total synthesis of (+)-goniodiol

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Publication details

The article was received on 23 Feb 2006, accepted on 09 Mar 2006 and first published on 27 Mar 2006


Article type: Paper
DOI: 10.1039/B602805E
Citation: Org. Biomol. Chem., 2006,4, 1698-1706
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    A highly enantioselective total synthesis of (+)-goniodiol

    E. W. Tate, D. J. Dixon and S. V. Ley, Org. Biomol. Chem., 2006, 4, 1698
    DOI: 10.1039/B602805E

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