Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/137247
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Type: | Journal article |
Title: | Total Synthesis of Atrachinenins A and B |
Author: | French, S.A. Sumby, C.J. Huang, D.M. George, J.H. |
Citation: | Journal of the American Chemical Society, 2022; 144(50):22844-22849 |
Publisher: | American Chemical Society |
Issue Date: | 2022 |
ISSN: | 0002-7863 1520-5126 |
Statement of Responsibility: | Sarah A. French, Christopher J. Sumby, David M. Huang, and Jonathan H. George |
Abstract: | Inspired by a new biosynthetic hypothesis, we report a biomimetic total synthesis of atrachinenins A and B that explains their racemic nature. The synthesis exploits an intermolecular Diels−Alder reaction between a quinone meroterpenoid and E-β-ocimene, followed by intramolecular (3 + 2) cycloaddition and a late-stage aerobic oxidation. Divergent transformations of a simple model system gave several complex polycyclic scaffolds, while also suggesting a structure revision for atrachinenin C. |
Keywords: | Quinones Biomimetics Cyclization Oxidation-Reduction Stereoisomerism Cycloaddition Reaction |
Rights: | © 2022 American Chemical Society |
DOI: | 10.1021/jacs.2c09978 |
Grant ID: | http://purl.org/au-research/grants/arc/DP200102964 |
Published version: | http://dx.doi.org/10.1021/jacs.2c09978 |
Appears in Collections: | Chemistry publications |
Files in This Item:
File | Description | Size | Format | |
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hdl_137247.pdf | Accepted version | 3.53 MB | Adobe PDF | View/Open |
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