Studies on synthesis of optically active twelve-membered diynes: a convergent construction of a twelve-membered diketodiyne compound with C2 symmetry

Abstract

A convergent procedure for the preparation of optically active twelve-membered diketodiyne derivatives with C₂ symmetry possessing four hydroxy functionalities was developed starting from the commercially available diethyl L-tartrate. The key step for the construction of the twelve-membered diyne framework involved an intramolecular chromous chloride-mediated coupling reaction between the aldehyde functionality and the alkyne moiety having an iodine atom at its terminus.