PART I: CONCISE, SCALABLE AND ENANTIOSELECTIVE TOTAL SYNTHESIS OF PROSTAGLANDINS PART II: PHOSPHINE-CATALYZED ENANTIOSELECTIVE [3+2] ANNULATION UTILIZING CYCLOPROPANE SUBSTRATES

Abstract

Prostaglandins are important natural products. Although important progresses have been made in the total synthesis of prostaglandins, the current synthesis of PGs still suffers from low yields and lengthy steps. Therefore, we developed a concise, scalable and enantioselective synthetic methodology for PGS by employing a key Zhang enyne cyclodimerizations. Organphosphines is one type of the most powerful nucleophilic Lewis base catalysts. Generally, the reaction partners in phosphine catalysis are activated alkene, alkyne, allene or MBH adducts. Cyclopropane derivatives are seldom used in this area. Therefore, we reported an unprecedented phosphine-catalyzed enantioselective [3+2] annulation utilizing racemic vinylcyclopropane.