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https://hdl.handle.net/2440/101494
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Type: | Journal article |
Title: | Some chemical speculation on the biosynthesis of corallidictyals A-D |
Author: | Markwell-Heys, A. George, J. |
Citation: | Organic and Biomolecular Chemistry, 2016; 14(24):5546-5549 |
Publisher: | Royal Society of Chemistry |
Issue Date: | 2016 |
ISSN: | 1477-0520 1477-0539 |
Statement of Responsibility: | Adrian W. Markwell-Heys and Jonathan H. George |
Abstract: | The efficient conversion of siphonodictyal B into the spirocyclic natural products corallidictyals A-D has been achieved via oxidative and acid catalyzed cyclizations. The oxidative cyclization of siphonodictyal B occured spontaneously under aerobic oxidation conditions, which suggests that corallidictyals A and B are possibly artefacts of the isolation process. The mechanism of the oxidative cyclization of siphonodictyal B could be described as either an anionic 5-endo-trig cyclization (which is formally disfavoured by Baldwin's rules), or as an electrocyclic reaction, of an ortho-quinone intermediate. |
Keywords: | Animals Porifera Sesquiterpenes Cyclization Oxidation-Reduction |
Rights: | This journal is © The Royal Society of Chemistry 2016 |
DOI: | 10.1039/c6ob00171h |
Grant ID: | http://purl.org/au-research/grants/arc/DP160103393 |
Published version: | http://dx.doi.org/10.1039/c6ob00171h |
Appears in Collections: | Aurora harvest 3 Chemistry publications |
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