Visible-light photoredox catalysis enables the biomimetic synthesis of nyingchinoids A, B, and D, and rasumatranin D
Files
(Accepted version)
Date
2019
Authors
Hart, J.D.
Burchill, L.
Day, A.J.
Newton, C.G.
Sumby, C.J.
Huang, D.M.
George, J.H.
Editors
Advisors
Journal Title
Journal ISSN
Volume Title
Type:
Journal article
Citation
Angewandte Chemie International Edition, 2019; 131(9):2817-2820
Statement of Responsibility
Jacob D. Hart, Laura Burchill, Aaron J. Day, Christopher G. Newton, Christopher J. Sumby, David M. Huang, and Jonathan H. George
Conference Name
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.
School/Discipline
Dissertation Note
Provenance
Description
German edition
Access Status
Rights
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim