An improved stereoselective total synthesis of (R)-rugulactone

A novel route for the stereoselective total synthesis of (R)-rugulactone 1 has been developed, starting from substituted epoxide 4 and 3-phenylpropionaldehyde 5 employing Julia-Kocienski olefination as a key step to construct E-configured alpha,beta-unsaturated keto-group. The overall yield of the synthesized rugulactone is 19.94% and is better than the reported methods. (C) 2011 Elsevier Ltd. All rights reserved.