A Stereocontrolled Synthesis of a Novel Prostacyclin Analog “Allene- Carbacyclin”. Application of Molecular Mechanics Calculations to Organic Synthesis.

Abstract The synthesis of a novel Prostacyclin/Carbacyclin analog 1a has been achieved in a stereocontrolled manner starting from the readily available bicyclic ketone 3 . A key strategic feature of the synthesis is a nucleophilic acetylide anion addition to 3 , the stereochemistry of which is predicted by MM2 calculations.