Open AccessDivergent Synthesis and Real-Time Biological Annotation of Optically Active Tetrahydrocyclopenta[c]pyranone Derivatives
Author(s) -
Shawn D. Nelson,
Mathias Wawer,
Stuart L. Schreiber
Publication year - 2016
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.6b03118
Subject(s) - chemistry , enantiomer , drug discovery , combinatorial chemistry , optically active , annotation , stereochemistry , computational biology , nanotechnology , computer science , organic chemistry , biochemistry , artificial intelligence , biology , materials science
Sp 3 -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.