Artemisinin (also known as Qinghaosu) is a peroxide-containing compound that has been
Chapter 14, Problem 14.72(choose chapter or problem)
Artemisinin (also known as Qinghaosu) is a peroxide-containing compound that has been used in traditional Chinese medicine as a treatment for malaria. Today, synthetic derivatives of artemisinin are standard treatments to fight against Plasmodium falciparum infections, the parasite which causes the most dangerous form of malaria. Epoxide 1 is a synthetic derivative of artemisinin; when treated with hexafluoro2-propanol and catalytic acid, it undergoes a ring-opening reaction for which the regiochemical outcome and stereochemical outcome are both contrary to what you might have expected (J. Org. Chem. 2002, 67, 12531260). Explain these observations with a plausible mechanism. O O O O H H O O O O O H H O cat. H3O+ F3C OH CF3 CH(CF3)2
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