volume 30, issue 43, Pno-no 2010
DOI: 10.1002/chin.199943198
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Peter Kapferer,
Francisco Sarabia,
Andrea Vasella

Abstract: ()-Valienamine (16) was prepared in seven steps and in an overall yield of 17% from commercially available 2,3,4,6-tetra-O-benzyl-d-glucopyranose. Stereoselective addition of vinylmagnesium bromide to the 1,3,4,5-tetra-O-benzyl-6,7-dideoxy-l-xylo-hept-6-en-2-ulose (2) gave diene 3 (86%). Ring-closing alkene metathesis of 3 in the presence of 0.15 equiv. of Grubbs catalyst 1 gave the cyclohexene 4 (58%), that was converted into ()-valienamine (16) in three steps and in 47% yield. Similarly, ring-closing alkene…

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