Small-molecule diversity using a skeletal transformation strategy |
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Authors: | Kumar Nilesh Kiuchi Masatoshi Tallarico John A Schreiber Stuart L |
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Institution: | Howard Hughes Medical Institute, Department of Chemistry and Chemical Biology, Harvard University, Broad Institute of Harvard and MIT, Cambridge, Massachusetts 02138, USA. |
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Abstract: | reaction: see text] We describe a short synthetic sequence resulting in >4000 skeletally diverse small molecules that have three distinct skeletal frameworks among other unique structural features. The sequence entails skeletal transformations pioneered by Winterfeldt and co-workers. We use epoxide ring openings and subsequent functionalizations that provide, e.g., spirocyclic oxazolidines, Lewis acid catalyzed Diels-Alder reactions of a steroid-derived diene that afford stable and isolable ring B adducts, and subsequent retro-Diels-Alder fragmentations that yield 14-membered paracyclophanes. |
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