Orthogonally protected diaminocyclopentenones as versatile synthons: Total synthesis of (±)-Agelastatin A

Natural products containing amicyclopentanes are common secondary metabolites, often biologically active. This works aims at the preparation of a useful synthon containing orthogonally protected amines. To this end, furfural and two amines were employed to form mixed trans-4,5-diaminocyclopentenones promoted by Cu(OTf)2. The selected amines can be orthogonally deprotected, allowing selective modification of the amines on the cyclopentane core. Their utility was showcased for the total synthesis of highly complex (±)-Agelastatin A.