Scientific Publications

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

Publication TypeJournal Article
AuthorsFitzgerald, ME, Mulrooney CA, Duvall JR, Wei J., Suh BC, Akella LB, Vrcic A., and Marcaurelle LA
AbstractA 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.
Year of Publication2012
JournalACS combinatorial science
Volume14
Issue2
Pages89-96
Date Published (YYYY/MM/DD)2012/02/13
ISSN Number2156-8952
DOI10.1021/co200161z
PubMedhttp://www.ncbi.nlm.nih.gov/pubmed/22252910?dopt=Abstract