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Organic letters DOI:10.1021/ol0504345

Small-molecule diversity using a skeletal transformation strategy.

Publication TypeJournal Article
Year of Publication2005
AuthorsKumar, N, Kiuchi, M, Tallarico, JA, Schreiber, SL
JournalOrganic letters
Volume7
Issue13
Pages2535-8
Date Published2005/06/23
ISSN1523-7060
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.

URLhttp://dx.doi.org/10.1021/ol0504345
DOI10.1021/ol0504345
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/15957884?dopt=Abstract