Scientific Publications

Small-molecule diversity using a skeletal transformation strategy.

Publication TypeJournal Article
AuthorsKumar, N., Kiuchi M., Tallarico JA, and Schreiber SL
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.
Year of Publication2005
JournalOrganic letters
Volume7
Issue13
Pages2535-8
Date Published (YYYY/MM/DD)2005/06/23
ISSN Number1523-7060
DOI10.1021/ol0504345
PubMedhttp://www.ncbi.nlm.nih.gov/pubmed/15957884?dopt=Abstract