Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 9, Pages 2791-2794Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814089
Keywords
biomimetic synthesis; cascade reactions; natural products; photoredox catalysis; total synthesis
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Funding
- Australian Research Council Future Fellowship [FT170100437]
- Australian Research Council [FT170100437] Funding Source: Australian Research Council
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The total synthesis of nyingchinoidsA 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.
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