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Synfacts 2020; 16(12): 1383
DOI: 10.1055/s-0040-1719534
DOI: 10.1055/s-0040-1719534
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (±)-Tronocarpine
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Significance
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.
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Comment
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.
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Publication History
Article published online:
17 November 2020
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