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Synfacts 2008(10): 1037-1037  
DOI: 10.1055/s-2008-1078155
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Benzopyridyloxepines Contain-
ing Stereodefined Exocyclic Double Bonds

Contributor(s): Victor Snieckus, Dmitry N. Korolev
M. W. Carson*, M. W. Giese, M. J. Coghlan
Eli Lilly and Co., Indianapolis, USA
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

Reported is a synthesis of benzo­pyridyloxepines containing geometrically pure exocyclic tetrasubstituted double bonds. The key steps are 1) a syn-stereoselective diboration of aryl alkynes using bispinacolatodiborane, 2) an intramolecular Suzuki cross-coupling reaction which occurs in stereo- and regiocontrolled fashion and 3) an intermolecular Suzuki-Miyaura cross-coupling to furnish the final tetrasubstituted olefinic benzopyridyloxepines.