Artemisinin analogs having antimalarial, antiproliferative, and antitumor activities and chemoselective methods of making the same

A method of producing a novel artemisinin analogue comprising:

• reacting artemisinin with an organolithium reagent that chemoselectively reacts at the C-10 position of artemisinin without disrupting the O—O bond to form a lithiated oxide at the C-10 position followed by adding a reagent that acetylates the C-10 oxide in situ to afford the intermediate (Ia) having the structure
• wherein R1 and R2 are hydrogen or together R1 and R2 form a benzene ring;
• treating said intermediate (Ia) with a reagent which eliminates HOAc from (Ia) to form the 9,10 alkene (Ib) having the structure
• wherein R1 and R2 are hydrogen or together R1 and R2 form a benzene ring;
• and
• converting said 9, 10 alkene (Ib) to enal (Ie) having the structure

A method for treating malaria comprising administering an effective amount of an artemisinin analog having the structure

• wherein R is
• (C═)OX wherein X is hydrogen, alkyl, alkenyl, alkynyl, aryl or heteroaryl,
• C(OH)X2 wherein X is alkyl, alkenyl, alkynyl, aryl or heteroaryl,
• alkyl,
• alkyl comprising one or more substituents,
• heteroalkyl,
• alkenyl,
• alkenyl comprising one or more substituents,
• alkynyl,
• aryl,
• aryl comprising one or more substituents,
• heteroaryl, or
• heteroaryl comprising one or more substituents,
• wherein said substituents are selected from a group comprising halogen, nitro, amino, hydroxy, thiohydroxy, lower alkoxy, lower thioalkyl, lower alkyl, NHC(═O)R1 is aryl or lower alkyl, COOH, or COOR2 wherein R2 is aryl or lower alkyl.