Copper(I) catalyzed conjugate addition of Grignard reagents to acrylic acids: Homologation of artemisinic acid and subsequent conversion to 9-substituted artemisinin analogs

Article abstract of DOI:10.1016/S0040-4039(97)01428-7

A new route to novel 9-substituted-10-deoxoartemisinin analogs (13, 14) was developed employing photoxygenation of homologated derivatives of artemisinic acid (9, 10). Conjugate addition to the acrylate moiety of artemisinic acid 2 was made possible by in situ protection as a silyl ester, Cu(I)-catalyzed 1,4-addition of RMgX, and deprotection.