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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 13
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Original Articles

A Convergent Synthesis of the O-Benzyl Derivative of Enantio-Ineupatoriol From a Carbohydrate Precursor

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Pages 1461-1474 | Published online: 03 Jan 2007

References

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  • This route leads via 7 to the enantiomer of the natural ineupatoriol. The expensive L-glucose enantiomer actually required for an analogous synthesis of ineupatoriol itself has been made more readily available by elegant recent syntheses from non-carbohydrate precursors by Sharpless, Masamune and Danishefsky7,8
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  • When this sequence was attempted using the much more expensive phenoxythiocarbonyl chloride reagent (PhOC(=S) Cl)11 to derivatize the alcohol, the overall yield was no better.
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  • While not important to the present synthesis the appearance of the very characteristic H-3 proton in the dithiocarbonate derivative 5b at δ 6.1 (q, J=3 Hz, 1H) strongly suggests an α (axial) configuration for the C-3 hydroxyl group.
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