ORGN 652 |
| Derivatives of pleuromutilin continue to be of interest due to their unique prokaryotic ribosomal binding properties which lead to high levels of antibacterial activity. A short route to the core of pleuromutilin could help identify a minimal scaffold needed to retain antibacterial activity. A direct 9 step approach to the functionalized propellane core of this natural product is described (Scheme 1). From known enone 1, a tandem cuprate addition/cyclocondensation reaction was used to establish hydrindenone 2. Further manipulations, which included hydrocyanation and asymmetric homopropargylation reactions, gave alkynal 3 as a single diastereomer. Various ring closing strategies were employed in an effort to obtain the propellane system (4).
|
|
Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |
