Natural products containing aminocyclopentanes are common
secondary
metabolites, often biologically active. This work aims at the preparation
of a useful synthon for total synthesis containing orthogonally protected
amines. To this end, furfural and two amines were employed to form
mixedtrans-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.