Cyclocitrinol featured a unique bridged bicyclic skeletons, which may be constructed via SmI 2 -mediated reaction from a highly strained norcarenone.Herein, using commercially available 19-hydroxy-androstane as starting material, the norcarenone intermediate was synthesized via a novel homoallylic carbocation rearrangement, which was transformed into the core of cyclocitrinols.
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Liu et al. (2014) studied this question.
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