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Natural Products Synthesis from Birch Bark. The triterpenes are a diverse class of widely distributed natural products derived from squalene. Various cyclization and subsequent rearrangement reactions produce many complex structural types with a wide divergence of biological properties. For example the pentacyclic triterpene, betulin, is isolated from white birch species, and its carboxylic acid derivative, betulinic acid, is currently being studied as a selective inhibitor of human melanoma, brain cancer, and HIV. In their laboratory article Isolation of Betulin and Rearrangement to Allobetulin, Green, Bentley, Chung, Lynch, and Jensenon describe how organic chemistry students can study a wide variety of reaction and NMR topics by extracting betulin from birch bark and then converting the isolated material to allobetulin.
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