The synthesis and properties of dialkyl epoxyhexahydrophthalates

Synthesis of the Madangamine Alkaloid Core by a C–C Bond Activation Cascade

“…To synthesize the epoxide we needed, anhydride 1 was first opened with benzyl alcohol in the presence of acid (Scheme ). The resulting cyclohexene 2 was then epoxidized with m -CPBA, which gave the desired diastereomer 3 as the major product . The treatment of this epoxide with sodium azide in the presence of cerium­(III) chloride gave the azidohydrin 4 , possessing the desired relative stereochemistry in ∼29% yield for the three-step sequence .…”