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ACS Comb Sci. 2012 Feb 13;14(2):89-96. doi: 10.1021/co200161z. Epub 2012 Jan 17.

Build/couple/pair strategy for the synthesis of stereochemically diverse macrolactams via head-to-tail cyclization.

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  • 1Chemical Biology Platform, Broad Institute of MIT and Harvard, Cambridge, Massachusetts 02142, United States.

Abstract

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.

PMID:
22252910
[PubMed - indexed for MEDLINE]
PMCID:
PMC3289975
Free PMC Article
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