Progress toward the synthesis of a conformationally constrained bicyclic amino acid, 2-carboxy-6-hydroxyoctahydroindole (Choi), is presented. The proposed five-step route begins with <i>tert-</i>butyl acrylate and ethyl 2-oxocyclohexanecarboxylate and employs α-amination at an early stage.  This approach may afford stereochemical flexibility, potentially yielding some of the many isomers not yet observed in nature.

Progress toward the synthesis of the heterocycle Choi

253rd National Meeting (2017)

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