Total synthesis of C31-methyl ketone apocarotenoids 2: The first total synthesis of (3R)-triophaxanthin

Abstract

Five possible synthetic strategies have been developed for the synthesis of (all-E)-(3R)-triophaxanthin. A short discussion of these strategies is presented. Fully characterised, optically active (all-E)-(3R)-triophaxanthin was prepared by total synthesis for the first time, with 9% overall yield, in 13 linear steps from the readily available (4R,6R)-actinol, (2E)-3-methyl-2-penten-4-yn-1-ol, (all-E)-2,7-dimethyl-2,4,6-octatrienedial and 1,1-dimethoxypropanone. © Acta Chemica Scandinavica 1997.