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Synfacts 2010(9): 1036-1036  
DOI: 10.1055/s-0030-1257953
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Application of Electrophile-Induced Ether Transfer in the Synthesis of Polyethers

Contributor(s): Mark Lautens, David A. Candito
K. Lui, J. W. Arico, R. E. Taylor*
University of Notre Dame, USA
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Publication History

Publication Date:
23 August 2010 (online)

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Significance

Isotactic polymethoxy-1-alkenes constitute a family of natural products that have attracted many synthetic attempts. The authors recently reported an electrophile-induced ether transfer for the stereoselective synthesis of poly-ketide structural units (K. Lui, R. E. Taylor, R. Kartika Org. Lett. 2006, 8, 5393). The ability to avoid protecting group ­manipulation, excellent stereoselectivity and the ­installation of a synthetic handle are noteworthy features of this methodology. The authors demonstrate the power of this approach in the convergent synthesis of tolypothrix hexaether.