Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A

Natural products containing aminocyclopentanes are commonsecondarymetabolites, often biologically active. This work aims at the preparationof a useful synthon for total synthesis containing orthogonally protectedamines. To this end, furfural and two amines were employed to formmixed trans-4,5-diaminocyclopentenones promoted byCu-(OTf)(2). The selected amines can be orthogonally deprotected,allowing selective modification of the amines on the cyclopentanecore. Their utility was showcased for the total synthesis of highlycomplex (+/-)-Agelastatin A.

Automated summary

This research aims to synthesize naturally occurring compounds with biologically active aminocyclopentanes and prepare a versatile synthon for total synthesis with orthogonal protection of amines. Mixed trans-4,5-diaminocyclopentenones were formed by reacting furfural and two amines using Cu-(OTf)(2) as a catalyst. The selected amines can be selectively deprotected, enabling selective modification of amines on the cyclopentane core. The significance of this research is demonstrated by the successful total synthesis of highly complex (+/-)-Agelastatin A.