title: Synthesis of stereochemically and skeletally diverse fused ring systems from functionalized C-glycosides.
abstract: A diversity-oriented synthesis (DOS) strategy was developed for the synthesis of stereochemically diverse fused-ring systems containing a pyran moiety. Each scaffold contains an amine and methyl ester for further diversification via amine capping and amide coupling. Scaffold diversity was evaluated in comparison to previously prepared scaffolds by a shape-based principal moments of inertia (PMI) analysis.
authors.affiliation: Chemical Biology Platform, The Broad Institute of Harvard and MIT, 7 Cambridge Center, Cambridge, Massachusetts 02142, United States.
authors.forename: Baudouin
authors.initials: B
authors.lastname: Gerard
authors.forename: Maurice D
authors.initials: MD
authors.lastname: Lee
authors.forename: Sivaraman
authors.initials: S
authors.lastname: Dandapani
authors.forename: Jeremy R
authors.initials: JR
authors.lastname: Duvall
authors.forename: Mark E
authors.initials: ME
authors.lastname: Fitzgerald
authors.forename: Sarathy
authors.initials: S
authors.lastname: Kesavan
authors.forename: Jason T
authors.initials: JT
authors.lastname: Lowe
authors.forename: Jean-Charles
authors.initials: JC
authors.lastname: Marié
authors.forename: Bhaumik A
authors.initials: BA
authors.lastname: Pandya
authors.forename: Byung-Chul
authors.initials: BC
authors.lastname: Suh
authors.forename: Morgan Welzel
authors.initials: MW
authors.lastname: O'Shea
authors.forename: Michael
authors.initials: M
authors.lastname: Dombrowski
authors.forename: Diane
authors.initials: D
authors.lastname: Hamann
authors.forename: Berenice
authors.initials: B
authors.lastname: Lemercier
authors.forename: Tiffanie
authors.initials: T
authors.lastname: Murillo
authors.forename: Lakshmi B
authors.initials: LB
authors.lastname: Akella
authors.forename: Michael A
authors.initials: MA
authors.lastname: Foley
authors.forename: Lisa A
authors.initials: LA
authors.lastname: Marcaurelle
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D011714:Pyrans