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Total Synthesis of (±)-Tronocarpine
Nakayama, Kamba and co-workers report a total synthesis of tronocarpine, a chippiine-type indole alkaloid containing an azabicyclo[3.3.1]nonane core. The synthesis features a tandem cyclization consisting of unsaturated aldehyde formation, intermolecular aldol reaction, and lactamization.
Indole D was obtained from known precursors in four steps. D gave rise to F and an inseparable mixture of G and H, which could be converted to F in one step. Tandem cyclization was achieved by subsequent treatment with Na2CO3 and Pd/CaCO3. Tronocarpine was obtained in two steps from K.
17 November 2020 (online)
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