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Synthesis of a stereochemically diverse library of medium-sized lactams and sultams via S(N)Ar cycloetherification.

Publication TypeJournal Article
AuthorsGerard, B., Duvall JR, Lowe JT, Murillo T., Wei J., Akella LB, and Marcaurelle LA
AbstractWe have implemented an aldol-based "build/couple/pair" (B/C/P) strategy for the synthesis of stereochemically diverse 8-membered lactam and sultam scaffolds via S(N)Ar cycloetherification. Each scaffold contains two handles, an amine and aryl bromide, for solid-phase diversification via N-capping and Pd-mediated cross coupling. A sparse matrix design strategy that achieves the dual objective of controlling physicochemical properties and selecting diverse library members was implemented. The production of two 8000-membered libraries is discussed including a full analysis of library purity and property distribution. Library diversity was evaluated in comparison to the Molecular Library Small Molecule Repository (MLSMR) through the use of a multifusion similarity (MFS) map and principal component analysis (PCA).
Year of Publication2011
JournalACS combinatorial science
Volume13
Issue4
Pages365-74
Date Published (YYYY/MM/DD)2011/07/11
ISSN Number2156-8952
DOI10.1021/co2000218
PubMedhttp://www.ncbi.nlm.nih.gov/pubmed/21526820?dopt=Abstract