Alpha-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 vitro testing of 5b for antimalarial activity.
Reference:
Van der Westhuyzen, CW and Parkinson, CJ. 2005. Synthesis of a structurally constrained endoperoxide having antimalarial activity from alpha-santonin. South African Journal of Chemistry, vol. 58, pp 41-45
Van der Westhuyzen, C. W., & Parkinson, C. (2005). Synthesis of a structurally constrained endoperoxide having antimalarial activity from alpha-santonin. http://hdl.handle.net/10204/763
Van der Westhuyzen, Christiaan W, and CJ Parkinson "Synthesis of a structurally constrained endoperoxide having antimalarial activity from alpha-santonin." (2005) http://hdl.handle.net/10204/763
Van der Westhuyzen CW, Parkinson C. Synthesis of a structurally constrained endoperoxide having antimalarial activity from alpha-santonin. 2005; http://hdl.handle.net/10204/763.
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