Enantioselective Synthesis of 2,3-Disubstituted Benzomorpholines: Analogues of Lignan Natural Products.

Abstract

The enantioselective synthesis of 2,3-disubstituted benzomorpholines, analogues of 1,4-benzodioxane natural products, has been achieved via addition of electron-rich aromatic donors to acyl-iminium ions derived from benzomorpholine aminols. Subsequent modification of the benzomorpholine scaffold allows side chains mimicking those found in 1,4-benzodioxane lignans to be added. Antiproliferative testing of the prepared analogues showed promising results against MDA-MB-231 and HCT116 cancer cell lines.