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https://hdl.handle.net/2440/106797
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Type: | Journal article |
Title: | Biomimetic total synthesis of (±)-verrubenzospirolactone |
Author: | Lam, H. Pepper, H. Sumby, C. George, J. |
Citation: | Angewandte Chemie International Edition, 2017; 56(29):8532-8535 |
Publisher: | Wiley |
Issue Date: | 2017 |
ISSN: | 1433-7851 1521-3773 |
Statement of Responsibility: | Hiu C. Lam, Henry P. Pepper, Christopher J. Sumby, and Jonathan H. George |
Abstract: | A five-step total synthesis of (±)-verrubenzospirolactone has been achieved using a biomimetic, intramolecular Diels-Alder reaction of a 2H-chromene to form two rings and four stereocenters in the final step. This Diels-Alder reaction occurs spontaneously at 30 °C "on-water", and thus suggests that it is likely to be non-enzymatic in nature. The structure of (±)-verrubenzospirolactone was also used to inspire a quadruple cascade reaction to generate seven stereocenters, four rings, three C-C bonds, and two C-O bonds in one step. |
Keywords: | Biomimetic synthesis; cycloaddition; natural products; terpenoids; total synthesis |
DOI: | 10.1002/anie.201700114 |
Grant ID: | http://purl.org/au-research/grants/arc/DP160103393 |
Published version: | http://dx.doi.org/10.1002/anie.201700114 |
Appears in Collections: | Aurora harvest 3 Chemistry publications |
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