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Studies on Biomimetic Singlet Oxygen Oxidations: Application to the Synthesis of the Alkaloid Simulenoline
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-6π-electrocyclization followed by a one-pot singlet-oxygen ene-reaction/r...
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Published in: | Journal of natural products (Washington, D.C.) D.C.), 2020-04, Vol.83 (4), p.1309-1313 |
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Main Author: | |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | 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-6π-electrocyclization followed by a one-pot singlet-oxygen ene-reaction/reduction sequence. New insights of singlet oxygen reactivity with olefinic substrates have been revealed. |
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ISSN: | 0163-3864 1520-6025 |
DOI: | 10.1021/acs.jnatprod.0c00210 |