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Synfacts 2020; 16(12): 1383
DOI: 10.1055/s-0040-1719534
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (±)-Tronocarpine

Rezensent(en):
Erick M. Carreira
,
Moritz J. Classen
Nakayama A, *, Nakamura T, Zaima T, Fujimoto S, Karanjit S, Namba K. * Tokushima University, Japan
Concise Total Synthesis of Tronocarpine.

Angew. Chem. Int. Ed. 2020;
DOI: 10.1002/anie.202009966.
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Key words

(±)-tronocarpine - chippiine alkaloids - tandem cyclization - Dess–Martin oxidation

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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Publikationsverlauf

Artikel online veröffentlicht:
17. November 2020

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