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Synfacts 2005(0): 0055-0055  
DOI: 10.1055/s-2005-869935
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Ring-Closing Metathesis to Build a Quaternary Carbon Center

Contributor(s): Mark Lautens, Y. Eric Fang
Y. Murakami, M. Shindo, K. Shishido*
University of Tokushima, Japan
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Publication History

Publication Date:
20 July 2005 (online)

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Significance

Diastereoselective ring-closing metathesis (RCM) was used to create a quaternary stereogenic center induced by protected hydroxyl groups. The initial stereogenic center was conveniently installed by Sharpless asymmetric epoxidation. The chiral RCM product cyclohexene was converted into a key chiral precursor used for the total synthesis of indole-containing alkaloid (-)-eburnamonine.