ORGN 696 |
| Diversity-oriented synthesis (DOS) uses principles of organic chemistry to rapidly access collections of diverse small molecules. Currently we are employing a DOS-based build/couple/pair algorithm to produce compound libraries possessing a high degree of stereochemical and skeletal diversity. Using this concept, we have generated a chiral linear amine template that has proven useful for the synthesis of a wide array of macrocycles and medium-sized rings by way of functional group pairing (FGP). In this report we present the preparation of a set of biaryl-containing macrocycles from this linear amine using an oxidative biaryl coupling as the key FGP step. From our chiral amine a bis-iodoaryl structure was prepared, and an oxidative biaryl coupling was performed by metal-halogen exchange with iPrMgCl, followed by transmetallation with Cu(I) and subsequent oxidation to release the biaryl. Eight stereoisomers of the macrocycle were generated and used to prepare a library of up to 1600 compounds. |
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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 |