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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
Statement of
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
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