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Conjugate addition to the acrylic acid moiety of artemisinic acid 2 was made possible by in situ protection as a silyl ester, treatment with a cyano-Gilman cuprate [Bu2CuLi·LiCN] to facilitate 1,4-addition, and deprotective workup affording the homologated carboxylic acid 9. Photoxygenation and acid treatment of 9 then led to the facile preparation of potent antimalarial 9-modified analogs of artemisinin.
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Vroman et al. (1998) studied this question.
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