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Small-molecule diversity using a skeletal transformation strategy.
| Publication Type | Journal Article |
| Authors | Kumar, 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 Publication | 2005 |
| Journal | Organic letters |
| Volume | 7 |
| Issue | 13 |
| Pages | 2535-8 |
| Date Published (YYYY/MM/DD) | 2005/06/23 |
| ISSN Number | 1523-7060 |
| DOI | 10.1021/ol0504345 |
| PubMed | http://www.ncbi.nlm.nih.gov/pubmed/15957884?dopt=Abstract |
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