Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/130744
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Type: | Journal article |
Title: | Visible-light photoredox catalysis enables the biomimetic synthesis of nyingchinoids A, B, and D, and rasumatranin D |
Author: | Hart, J.D. Burchill, L. Day, A.J. Newton, C.G. Sumby, C.J. Huang, D.M. George, J.H. |
Citation: | Angewandte Chemie International Edition, 2019; 131(9):2817-2820 |
Publisher: | Wiley |
Issue Date: | 2019 |
ISSN: | 0044-8249 1521-3757 |
Statement of Responsibility: | Jacob D. Hart, Laura Burchill, Aaron J. Day, Christopher G. Newton, Christopher J. Sumby, David M. Huang, and Jonathan H. George |
Abstract: | The total synthesis of nyingchinoids A and B has been achieved through successive rearrangements of a 1,2-dioxane intermediate that was assembled using a visible-light photoredox-catalysed aerobic [2+2+2] cycloaddition. Nyingchinoid D was synthesised with a competing [2+2] cycloaddition. Based on NMR data and biosynthetic speculation, we proposed a structure revision of the related natural product rasumatranin D, which was confirmed through total synthesis. Under photoredox conditions, we observed the conversion of a cyclobutane into a 1,2-dioxane through retro-[2+2] cycloaddition followed by aerobic [2+2+2] cycloaddition. |
Keywords: | Biomimetic synthesis; cascade reactions; natural products; photoredox catalysis; total synthesis |
Description: | German edition |
Rights: | © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
DOI: | 10.1002/ange.201814089 |
Grant ID: | http://purl.org/au-research/grants/arc/FT170100437 |
Published version: | http://dx.doi.org/10.1002/ange.201814089 |
Appears in Collections: | Aurora harvest 4 Chemistry and Physics publications |
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hdl_130744.pdf | Accepted version | 879.38 kB | Adobe PDF | View/Open |
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