Small-Molecule Diversity Using a Skeletal Transformation Strategy

Autor: Kumar, N., Kiuchi, M., Tallarico, J. A., Schreiber, S. L.
Zdroj: Organic Letters; June 2005, Vol. 7 Issue: 13 p2535-2538, 4p
Abstrakt: 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.
Databáze: Supplemental Index