A 12-step synthesis of the natural product (+)-Artemisinin, very active against malaria, is described. (-)-Isopulegol, which already contains two of the asymmetric centers of (+)-Artemisinin in the correct absolute configuration, was used as starting material.
The behavior of several epoxides when treated with NbCl5 was studied. In general, the studied epoxides reacted rapidly with NbCl5, giving, in most cases, more than one product (chlorohydrins, products containing solvent residues, as well as rearrangement products). A detailed study was performed to verify the effects of the temperature (rt, 0°C, or −78°C) and of the NbCl5 molar concentration on the composition of the products, yield, and time required for the reactions.
Epoxide ring opening is a frequently required transformation in Organic Synthesis. In this paper we describe the application of NbCl5 for this purpose using three different substrates. Chlorohydrins, 1,2-diols, products containing solvent residues as well as rearrangement products are obtained, depending on both the substrate structure and reaction conditions. Rationalizations to account for some of the results are suggested.