Efficient Preparation of Novel Qinghaosu (Artemisinin) Derivatives: Conversion of Qinghao (Artemisinic) Acid into Deoxoqinghaosu Derivatives and 5-Carba-4-deoxoartesunic Acid1

Richard K. Haynes; Simone C. Vonwiller

doi:10.1055/s-1992-21384

Synlett 1992; 1992(6): 481-483
DOI: 10.1055/s-1992-21384

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Efficient Preparation of Novel Qinghaosu (Artemisinin) Derivatives: Conversion of Qinghao (Artemisinic) Acid into Deoxoqinghaosu Derivatives and 5-Carba-4-deoxoartesunic Acid¹

Richard K. Haynes^* , Simone C. Vonwiller

^*Department of Organic Chemistry, The University of Sydney, New South Wales 2006, Australia

Abstract

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Qinghao acid (1) is converted via dihydroqinghao aldehyde (6) into secondary alcohols, each of which upon photooxygenation followed by treatment with copper(II) trifluoromethanesulfonate in dichloromethane-acetonitrile under oxygen in a "one-pot" operation affords ethyldeoxoqinghaosu (10), phenyldeoxoqinghaosu (11), allyldeoxoqinghaosu (12) and the β- and α-epimers 17 and 18 of 5-carba-4-deoxoartesunic acid, novel carbon analogues of artesunate.

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