Total Synthesis of the Proposed Structure of Indolyl 1,2-Propanediol Alkaloid, 1-(1<i>H</i>-Indol-3-yloxy)propan-2-ol

Abstract

The first total synthesis of the proposed structure of unprecedented indolyl derivative bearing 1,2-propanediol moiety is described. Isomerization of 3-alkoxyindolines through indolenium intermediates was the key step in the total synthesis. 1H, 13C-NMR, IR, and HRMS spectra of the synthetic compound drastically differed to those of the originally reported structure, which suggests the natural product requires revision.

Keywords

• 1-(1<i>H</i>-indol-3-yloxy)propan-2-ol
• indole alkaloid
• isomerization
• silver
• umpolung