title: Divergent Synthesis and Real-Time Biological Annotation of Optically Active Tetrahydrocyclopenta[c]pyranone Derivatives.
abstract: Sp3-rich compounds are underrepresented in libraries for probe- and drug-discovery, despite their promise of extending the range of accessible molecular shapes beyond planar geometries. With this in mind, a collection of single-enantiomer bicyclic, fused cyclopentenones underpinned by a complexity-generating Pauson-Khand cyclization was synthesized. A fingerprint of biological actions of these compounds was determined immediately after synthesis using real-time annotation-a process relying on multiplexed measurements of alterations in cell morphological features.
authors.affiliation: Howard Hughes Medical Institute and Center for the Science of Therapeutics, The Broad Institute of Harvard and MIT , 415 Main Street, Cambridge, Massachusetts 02142, United States.|Department of Chemistry & Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States.
authors.forename: Shawn D
authors.initials: SD
authors.lastname: Nelson
authors.affiliation: Howard Hughes Medical Institute and Center for the Science of Therapeutics, The Broad Institute of Harvard and MIT , 415 Main Street, Cambridge, Massachusetts 02142, United States.|Department of Chemistry & Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States.
authors.forename: Mathias J
authors.initials: MJ
authors.lastname: Wawer
authors.affiliation: Howard Hughes Medical Institute and Center for the Science of Therapeutics, The Broad Institute of Harvard and MIT , 415 Main Street, Cambridge, Massachusetts 02142, United States.|Department of Chemistry & Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States.
authors.forename: Stuart L
authors.identifier: 0000-0003-1922-7558
authors.initials: SL
authors.lastname: Schreiber
mesh_terms: D002452:Cell Count; D045744:Cell Line, Tumor; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008968:Molecular Conformation; D061848:Optical Imaging; D011753:Pyrones / Q000138:chemical synthesis* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D011753:Pyrones; C013905:cyclopentenone