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EC Number Reaction Commentary Reference
Show all pathways known for 4.2.1.125Display the word mapDisplay the reaction diagram Show all sequences 4.2.1.125dammarenediol II = (3S)-2,3-epoxy-2,3-dihydrosqualene + H2O an unusually complex and flexible reaction mechanism generates this ring system. As a general mechanism, firstly (3S)-2,3-oxidosqualene adopts a preorganized chair-chair-chair conformation, and activated by cationic attack. Then the oxirane ring of (3S)-2,3-oxidosqualene opens, following with a cascade of cation-olefin cyclizations, and generates a cyclic C-20 dammarenyl cation 748118
Show all pathways known for 4.2.1.125Display the word mapDisplay the reaction diagram Show all sequences 4.2.1.125dammarenediol II = (3S)-2,3-epoxy-2,3-dihydrosqualene + H2O cyclization initiated by protonation at the oxirane ring proceeds to form tetracycles. The resulting dammarenyl cation is trapped by stereospecific addition of water at C20 without further rearrangement 683213
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