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An Intra/Intermolecular Suzuki Sequence to Benzopyridyloxepines Containing Geometrically Pure Exocyclic Tetrasubstituted Alkenes

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journal contribution
posted on 03.07.2008, 00:00 by Matthew W. Carson, Matthew W. Giese, Michael J. Coghlan
A route to enable the preparation of 5-benzylidenyl-benzopyridyloxepine analogues was developed to continue our research in the field of nuclear hormone receptor modulators. The key steps are1) a syn-stereoselective diboration of a tethered aryl alkyne; 2) an intramolecular Suzuki cross-coupling reaction, which forms in a stereo- and regiocontrolled fashion, the 5-exoalkylidenyl 7-membered ring imbedded within the core of the scaffold and; 3) an intermolecular Suzuki to furnish the final tetra-substituted olefinic benzopyridyloxepines.