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. 2008 Jan 17;10(2):257-9.
doi: 10.1021/ol702651s. Epub 2007 Dec 13.

Total synthesis of (3R,9R,10R)-panaxytriol via tandem metathesis and metallotropic [1,3]-shift as a key step

Affiliations

Total synthesis of (3R,9R,10R)-panaxytriol via tandem metathesis and metallotropic [1,3]-shift as a key step

Eun Jin Cho et al. Org Lett. .

Abstract

Enyne metathesis is unique for its capacity to carry out multiple bond formation in tandem fashion. Its combined use with metallotropic [1,3]-shift allowed for the development of a novel strategy for the total synthesis of a conjugated 1,3-diyne-containing natural product (3R,9R,10R)-panaxytriol.

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Figures

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References

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