J Org Chem 2012 Nov 8;77(22):10010-20. Epub 2012 Nov 8.
Division of Crop Protection Chemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
The first total synthesis of curvularides A-E, isolated from a culture broth of the endophytic fungus Curvularia geniculata, is described. The divergent total synthesis reported herein confirmed the absolute configurations of curvularides A-E and supported that these natural products might be obtained from a common biosynthetic pathway. The key steps involved in the synthesis were the diastereoselective hydrogenation of exo-methylene-?-butyrolactone to ?-methyl-?-butyrolactone, Sharpless kinetic resolution, Sharpless asymmetric epoxidations, and intramolecular and intermolecular epoxide openings.