Visible-Light Photoredox Catalysis Enables the Biomimetic Synthesis of Nyingchinoids A, B, and D, and Rasumatranin D

Jacob D. Hart; Laura Burchill; Aaron J. Day; Christopher G. Newton; Christopher J. Sumby; David M. Huang; Jonathan H. George

doi:10.1002/anie.201814089

Visible-Light Photoredox Catalysis Enables the Biomimetic Synthesis of Nyingchinoids A, B, and D, and Rasumatranin D

Jacob D. Hart, Laura Burchill, Aaron J. Day, Christopher G. Newton, Christopher J. Sumby, David M. Huang, Jonathan H. George

Research output: Contribution to journal › Article › Research › peer-review

31 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2791-2794
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	9
DOIs	https://doi.org/10.1002/anie.201814089
Publication status	Published - 25 Feb 2019
Externally published	Yes

Keywords

biomimetic synthesis
cascade reactions
natural products
photoredox catalysis
total synthesis

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10.1002/anie.201814089

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title = "Visible-Light Photoredox Catalysis Enables the Biomimetic Synthesis of Nyingchinoids A, B, and D, and Rasumatranin D",

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",

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AU - Hart, Jacob D.

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AU - Day, Aaron J.

AU - Newton, Christopher G.

AU - Sumby, Christopher J.

AU - Huang, David M.

AU - George, Jonathan H.

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KW - cascade reactions

KW - natural products

KW - photoredox catalysis

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Visible-Light Photoredox Catalysis Enables the Biomimetic Synthesis of Nyingchinoids A, B, and D, and Rasumatranin D

Abstract

Keywords

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