A stereoselective synthesis, of artemisinin 11 base8 on intramolecular Diels-Alder reaction of the triene 4 derived from (+)isolimonene 2 is described.
Recently there has been a considerable interest in the chemistry 1 and total synthesis 2 of artemisinin, a promising antimalarial compound of Chinese origin isolated from the plant Artemisia annua L. This is -mainly due to its effectiveness in the treatment of drug resistant strains of malaria and also due to its synthetically challenging structure. Unlike other antimalarials it does not contain nitrogen but possesses a tetracyclic structure with peroxide bridge. Considering the potential of artemisinin and/or its derivatives in antimalarial therapy, we wanted to pursue a design of synthesis which should be more practical and stereospecific than any2 so far reported. This paper describes a stereoselective synthesis of artemisinin via intramolecular Diels-Alder approach. The starting material is (+)-isolinenene2 which in turn can easily be derived from (+)car-3-ene