Journal
JOURNAL OF NATURAL PRODUCTS
Volume 83, Issue 4, Pages 1309-1313Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.0c00210
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Funding
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET, PUE-2016)
- Agencia Nacional de Promocion Cientifica y Tecnologica (ANPCyT) [PICT-2014-0408, PICT-2017-2694]
- Agencia Santafesina de Ciencia, Tecnologia e Innovacion (ASACTEI) [AC-2015-00005]
- Universidad Nacional de Rosario [BIO 580]
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The synthesis of the biologically active alkaloid simulenoline, isolated from the roots of Zanthoxylum simulans, is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6-pelectrocyclization followed by a one-pot singlet-oxygen enereaction/reduction sequence. New insights of singlet oxygen reactivity with olefinic substrates have been revealed.
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