Visible-Light Photoredox Catalysis Enables the Biomimetic Synthesis of Nyingchinoidsâ
A, B, and D, and Rasumatraninâ
D.
Angew Chem Int Ed Engl
; 58(9): 2791-2794, 2019 02 25.
Article
in En
| MEDLINE
| ID: mdl-30648330
ABSTRACT
The total synthesis of nyingchinoidsâ
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. Nyingchinoidâ
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 rasumatraninâ
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.
Key words
Full text:
1
Database:
MEDLINE
Main subject:
Terpenes
/
Biomimetic Materials
/
Light
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2019
Type:
Article
Affiliation country:
Australia