WHEN ORGANICS FAIL, TRY WATER

Abstract

BY REPLACING organic solvents with water, chemists have found a simple route to selectively make ladder polyethers, including the building blocks of notorious toxins, via an epoxide-opening cascade reaction ( Science 2007 ,317, 1189). Complex ladder polyether natural products, so named for their runglike structure, are the active toxins found in the harmful algal blooms known as red tides. Red tides cause devastating ecological damage, so scientists hope that by studying this water-promoted cascade reaction, they will gain a better understanding of how and why these toxins form. finding also offers a solution to what had been a long-standing puzzle for synthetic chemists. Twenty years ago, Koji Nakanishi, a chemistry professor at Columbia University, suggested that ladder polyether natural products arose biosynthetically from an elaborate cascade of epoxide-opening reactions that zip up the polyether structure. The Nakanishi hypothesis is very intellectually appealing, says Timothy F. Jamison, a Mas...