1990 Volume 38 Issue 6 Pages 1775-1777
In the presence of cesium fluoride, the Claisen rearrangement of aryl propargyl ethers selectively provided 2-methylbenzofurans, which was successively treated with osmium tetroxide, periodic acid and 5% sodium hydroxide to give salicylaldehydes in good yields. The method was used to synthesize chelerythrine (2) via the common intermediate (8) prepared by the two routes as shown in Chart 3.