Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/106797
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DC Field | Value | Language |
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dc.contributor.author | Lam, H. | - |
dc.contributor.author | Pepper, H. | - |
dc.contributor.author | Sumby, C. | - |
dc.contributor.author | George, J. | - |
dc.date.issued | 2017 | - |
dc.identifier.citation | Angewandte Chemie International Edition, 2017; 56(29):8532-8535 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.issn | 1521-3773 | - |
dc.identifier.uri | http://hdl.handle.net/2440/106797 | - |
dc.description.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. | - |
dc.description.statementofresponsibility | Hiu C. Lam, Henry P. Pepper, Christopher J. Sumby, and Jonathan H. George | - |
dc.language.iso | en | - |
dc.publisher | Wiley | - |
dc.source.uri | http://dx.doi.org/10.1002/anie.201700114 | - |
dc.subject | Biomimetic synthesis; cycloaddition; natural products; terpenoids; total synthesis | - |
dc.title | Biomimetic total synthesis of (±)-verrubenzospirolactone | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1002/anie.201700114 | - |
dc.relation.grant | http://purl.org/au-research/grants/arc/DP160103393 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Sumby, C. [0000-0002-9713-9599] | - |
dc.identifier.orcid | George, J. [0000-0002-7330-2160] | - |
Appears in Collections: | Aurora harvest 3 Chemistry publications |
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