Stereoselective total synthesis of (+)-artemisinin, the antimalarial constituent of Artemisia annua L

…, WKM Chong, C Jennings-White

Index: Avery; Chong; Jennings-White Journal of the American Chemical Society, 1992 ,  vol. 114,  # 3  p. 974 - 979

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Citation Number: 227

Abstract

Abstract: A 10-step stereoselective total synthesis of the antimalarial cadinane sesquiterpene (+)-artemisinin (1) is described. Elaboration of (R)-(+)-pulegone to the known sulfoxide 11 was followed by dianion alkylation and desulfurization to provide the trans-2, 3- subtituted cyclohexanone 7. Homologation to the cyclohexenecarboxaldehyde 6 was followed by a diastereoselective silyl anion addition to afford the silyl acetate 15. Tandem ...