Polymer-bound haloate(I) anions by iodine(III)-mediated oxidation of polymer-bound iodide: Synthetic utility in natural product transformations

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Kirschning, A.; Kunst, E.; Ries, M.; Rose, L.; Schönberger, A.; Wartchow, R.: Polymer-bound haloate(I) anions by iodine(III)-mediated oxidation of polymer-bound iodide: Synthetic utility in natural product transformations. In: Arkivoc 2003 (2003), Nr. 6, S. 145-163

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A set of polymer-attached hypervalent iodate(I) complexes were prepared from polymer-bound iodide anion by ligand transfer of acetate and trifluoro acetate present in the corresponding iodine(III) reagents onto the iodide anion. The synthetic versatility of these polymer-bound reagents in terms of efficacy and ease of workup is demonstrated for selected examples in natural product synthesis and natural product derivatization. Thus, iodoacetoxylation of glycals is the initial step for the preparation of two deoxygenated disaccharides which are part of the carbohydrate units of the landomycins. In a second example, a one-pot multistep rearrangement of the decanolide decarestrictine D backbone is shown which is initiated by iodotrifluoroacylation of the olefinic double bond.
License of this version: CC BY-NC 3.0 Unported
Document Type: Article
Publishing status: publishedVersion
Issue Date: 2003
Appears in Collections:Naturwissenschaftliche Fakultät

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1 image of flag of Germany Germany 63 61.76%
2 image of flag of United States United States 10 9.80%
3 image of flag of China China 7 6.86%
4 image of flag of Mexico Mexico 4 3.92%
5 image of flag of Hungary Hungary 4 3.92%
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7 image of flag of United Kingdom United Kingdom 2 1.96%
8 image of flag of Kenya Kenya 1 0.98%
9 image of flag of Iran, Islamic Republic of Iran, Islamic Republic of 1 0.98%
10 image of flag of Bulgaria Bulgaria 1 0.98%
    other countries 5 4.90%

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