Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C3-building block

Herein we present the synthesis of the anhydrophytosphingosine jaspine B and three of its stereoisomers using a carbohydrate-derived alkoxyallene in order to obtain the products in enantiopure form. Key step of the reaction sequence is the addition of the lithiated alkoxyallene to pentadecanal, sett...

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Published inBeilstein journal of organic chemistry Vol. 9; no. 1; pp. 2564 - 2569
Main Authors Schmiedel, Volker Martin, Stefani, Stefano, Reissig, Hans-Ulrich
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 19.11.2013
Subjects
Chemistry
chiral auxiliaries
Full Research Paper
gold catalysis
jaspine B
lithiated alkoxyallenes
natural product synthesis
pachastrissamine
tetrahydrofurans
jaspine B
lithiated alkoxyallenes
chiral auxiliaries
tetrahydrofurans
gold catalysis
natural product synthesis
pachastrissamine
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Summary:Herein we present the synthesis of the anhydrophytosphingosine jaspine B and three of its stereoisomers using a carbohydrate-derived alkoxyallene in order to obtain the products in enantiopure form. Key step of the reaction sequence is the addition of the lithiated alkoxyallene to pentadecanal, setting the configuration at the later C-2 of the ring system. This reaction step proceeds with moderate selectivity and therefore leads to a stereodivergent approach to the natural product and its enantiomer. The gold-catalyzed 5-endo-cyclization affords the corresponding dihydrofurans, which after separation, azidation of the enol ether moiety and two subsequent reduction steps give the natural product and its stereoisomers.
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.9.291