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

被引：27

作者：

Hart, Jacob D. ^{[1
]}

Burchill, Laura ^{[1
]}

Day, Aaron J. ^{[1
]}

Newton, Christopher G. ^{[1
]}

Sumby, Christopher J. ^{[1
]}

Huang, David M. ^{[1
]}

George, Jonathan H. ^{[1
]}

机构：

[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 09期

基金：

澳大利亚研究理事会;

关键词：

biomimetic synthesis; cascade reactions; natural products; photoredox catalysis; total synthesis; ELECTRON-TRANSFER PHOTOOXYGENATION; OXYGENATED POLYKETIDES; 1,4-RADICAL CATION; 2+2 CYCLOADDITION; NATURAL-PRODUCTS; OMEGA-BIS(DIARYLETHENYL)ALKANES; METABOLITES; CYCLIZATION; CASCADE;

D O I：

10.1002/anie.201814089

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：2791 / 2794

页数：4

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