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ACS combinatorial science DOI:10.1021/co200161z

Build/Couple/Pair Strategy for the Synthesis of Stereochemically Diverse Macrolactams via Head-to-Tail Cyclization.

Publication TypeJournal Article
Year of Publication2012
AuthorsFitzgerald, ME, Mulrooney, CA, Duvall, JR, Wei, J, Suh, BC, Akella, LB, Vrcic, A, Marcaurelle, LA
JournalACS combinatorial science
Date Published2012/02/13

A build/couple/pair (B/C/P) strategy was employed to generate a library of 7936 stereochemically diverse 12-membered macrolactams. All 8 stereoisomers of a common linear amine precursor were elaborated to form the corresponding 8 stereoisomers of two regioisomeric macrocyclic scaffolds via head-to-tail cyclization. Subsequently, these 16 scaffolds were further diversified via capping of two amine functionalities on SynPhase Lanterns. Reagents used for solid-phase diversification were selected using a sparse matrix design strategy with the aim of maximizing coverage of chemical space while adhering to a preset range of physicochemical properties.