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Synfacts 2007(10): 1007-1007  
DOI: 10.1055/s-2007-968950
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Ratanhine

Contributor(s): Philip Kocienski, Stewart Eccles
E. P. Gillis, M. D. Burke*
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
07 November 2007 (online)

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Significance

Haloboronic acids protected with trivalent N-methyliminodiacetic acid ligands (e.g. A) undergo iterative Suzuki-Miyaura couplings because the protecting group induces boron pyramidalization that inhibits cross-coupling. Six examples are given along with an application to the synthesis of ratanhine.