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Issue 47, 2012
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Diastereoselective synthesis of the C17–C30 fragment of amphidinol 3

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Abstract

The diastereoselective synthesis of the C17–C30 fragment of amphidinol 3 (AM3) 1 was achieved from the enantio-enriched aldehyde 20, Weinreb amide 14 and 2-bromo-3-(trimethylsilyl)propene, which was used as a bifunctional conjunctive reagent. The absolute configuration of the stereogenic centers, in both aldehyde 20 and Weinreb amide 14, were efficiently controlled by using (+)-(R)-methyl-p-tolylsulfoxide as the unique source of chirality.

Graphical abstract: Diastereoselective synthesis of the C17–C30 fragment of amphidinol 3

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Supplementary files

Article information


Submitted
17 Aug 2012
Accepted
12 Oct 2012
First published
16 Oct 2012

Org. Biomol. Chem., 2012,10, 9418-9428
Article type
Paper

Diastereoselective synthesis of the C17–C30 fragment of amphidinol 3

N. Rival, D. Hazelard, G. Hanquet, T. Kreuzer, C. Bensoussan, S. Reymond, J. Cossy and F. Colobert, Org. Biomol. Chem., 2012, 10, 9418
DOI: 10.1039/C2OB26641E

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