AN APPROACH TOWARD THE OPHIOBOLANE SESTERTERPENES - SYNTHESIS OF THE CEROPLASTIN NUCLEUS

A stereocontrolled route to the 5-8-5 fused-ring nucleus of the ophiobolane sesterterpenes is presented. A McMurry coupling of an appropriately configured dicyclopentane system afforded the ceroplastin nucleus. Stereoselective hydrogenation reactions were used to set the requisite stereochemistry of the A/B and B/C ring junctures. © 1990, American Chemical Society. All rights reserved.