Synthesis of a Structurally Constrained Endoperoxide having Antimalarial Activity from -Santonin
Abstractα-Santonin 3 was successfully converted into a biologically active compound 5b containing an endoperoxide group through a photo-oxygenation approach as a single isomer. It was found that the singlet oxygen afforded the isomer produced by attack from the sterically-hindered face of cyclohexadiene derivative 4. Evidence to this end is presented based on NOE results and the products formed in the photo-oxygenation reaction, as well as the in vitrotesting of 5b for antimalarial activity.
Keywords: Santonin, endoperoxide, photo-oxygenation, singlet oxygen.
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