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  • Title: Small-molecule diversity using a skeletal transformation strategy.
    Author: Kumar N, Kiuchi M, Tallarico JA, Schreiber SL.
    Journal: Org Lett; 2005 Jun 23; 7(13):2535-8. PubMed ID: 15957884.
    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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