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

Abstract:

:We 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).

journal_name

ACS Comb Sci

authors

Gerard B,Duvall JR,Lowe JT,Murillo T,Wei J,Akella LB,Marcaurelle LA

doi

10.1021/co2000218

subject

Has Abstract

pub_date

2011-07-11 00:00:00

pages

365-74

issue

4

eissn

2156-8952

issn

2156-8944

journal_volume

13

pub_type

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