Concepedia

Direct conversion of pyranose anomeric OH→F→R in the artemisinin family of antimalarial trioxanes

Soon Hyung Woo, Michael H. Parker, Poonsakdi Ploypradith, John Northrop, Gary H. Posner

Tetrahedron Letters · 1998 · 37 citations · 16 references

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Concepts

Abstract

Eleven examples form the basis of a short and effective synthetic method for replacement of an anomeric fluorine atom by saturated, unsaturated, aryl and heteroaryl carbon nucleophiles to prepare α- or β-oriented C10-R derivatives of the trioxane 10-deoxoartemisinin.

References

16

From Qinghao, Marvelous Herb of Antiquity, to the Antimalarial Trioxane Qinghaosuand Some Remarkable New Chemistry

Richard K. Haynes, Simone C. Vonwiller · Accounts of Chemical Research · 1997 · 217 citations

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A convenient, one-step, high-yield replacement of an anomeric hydroxyl group by a fluorine atom using dast. Preparation of glycosyl fluorides.

Gary H. Posner, Stephen R. Haines · Tetrahedron Letters · 1985 · 197 citations

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Total Synthesis of the Antimalarial Sesquiterpene Peroxide Qinghaosu and Yingzhaosu A

Wei‐Shan Zhou, Xingxiang Xu · Accounts of Chemical Research · 1994 · 145 citations

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The Chemistry of C-Glycosides

Timothy Gallagher · Carbohydrate Research · 1996 · 97 citations

, , +10

Evidence for the Importance of High-Valent FeO and of a Diketone in the Molecular Mechanism of Action of Antimalarial Trioxane Analogs of Artemisinin

Gary H. Posner, Sheldon B. Park, Lluı̈sa González et al. · Journal of the American Chemical Society · 1996 · 92 citations

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