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

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

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

Author(s) -

Hart Jacob D.,

Burchill Laura,

Day Aaron J.,

Newton Christopher G.,

Sumby Christopher J.,

Huang David M.,

George Jonathan H.

Publication year - 2019

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201814089

Subject(s) - photoredox catalysis , visible spectrum , catalysis , nanotechnology , chemistry , materials science , photocatalysis , optoelectronics , organic chemistry

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.

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