首页|Synthesis of polyhydroxylated bicyclic tetrahydrofurans and tetrahydropyrans via a stereoselective domino cyclization/reduction reaction
Synthesis of polyhydroxylated bicyclic tetrahydrofurans and tetrahydropyrans via a stereoselective domino cyclization/reduction reaction
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NSTL
Elsevier
<![CDATA[<ce:abstract xmlns:ce="http://www.elsevier.com/xml/common/dtd" xmlns="http://www.elsevier.com/xml/ja/dtd" class="graphical" xml:lang="en" id="ab005" view="all"><ce:section-title id="st005">Graphical abstract</ce:section-title><ce:abstract-sec id="as005" view="all"><ce:simple-para>Display Omitted</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract xmlns:ce="http://www.elsevier.com/xml/common/dtd" xmlns="http://www.elsevier.com/xml/ja/dtd" class="author" xml:lang="en" id="ab010" view="all"><ce:section-title id="st010">Abstract</ce:section-title><ce:abstract-sec id="as010" view="all"><ce:simple-para id="sp0010" view="all">A novel reaction cascade involving a Lewis acid-induced migration of an isopropylidene protecting group followed by the formation of a pyranose or furanose ring and subsequent reduction of the hemiacetal is described. Depending on the reaction conditions, as well as, the stereochemistry of the substrate, polyhydroxylated tetrahydrofurans or tetrahydropyrans can be obtained in reasonable yields. The synthons used in this transformation were prepared via a highly stereoselective one-pot tandem reaction, consisting of a 1,4-Michael addition of vinylmagnesium bromide to<ce:small-caps>d</ce:small-caps>-glucose-derived cyclohexenone followed by aldol reaction with 2,3-<ce:italic>O</ce:italic>-isopropylidene-<ce:small-caps>d</ce:small-caps>-glyceraldehyde.</ce:simple-para></ce:abstract-sec></ce:abstract>]]>
Micha? Malik、Piotr Cmoch、Mykhaylo A. Potopnyk、S?awomir Jarosz
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Institute of Organic Chemistry, Polish Academy of Sciences
NSTL
Elsevier
