Details
| Original language | English |
|---|---|
| Pages (from-to) | 145-163 |
| Number of pages | 19 |
| Journal | Arkivoc |
| Volume | 2003 |
| Issue number | 6 |
| Publication status | Published - 2003 |
Abstract
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.
Keywords
- Decanolide, Glycosides, Hypervalent iodine reagents, Natural products, Polymer-bound reagents, Rearrangement
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Arkivoc, Vol. 2003, No. 6, 2003, p. 145-163.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Polymer-bound haloate(I) anions by iodine(III)-mediated oxidation ofpolymer-bound iodide
T2 - Synthetic utility in natural product transformations
AU - Kirschning, Andreas
AU - Kunst, Eike
AU - Ries, Monika
AU - Rose, Lars
AU - Schönberger, Andreas
AU - Wartchow, Rudolf
PY - 2003
Y1 - 2003
N2 - 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.
AB - 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.
KW - Decanolide
KW - Glycosides
KW - Hypervalent iodine reagents
KW - Natural products
KW - Polymer-bound reagents
KW - Rearrangement
UR - http://www.scopus.com/inward/record.url?scp=3242738280&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:3242738280
VL - 2003
SP - 145
EP - 163
JO - Arkivoc
JF - Arkivoc
SN - 1424-6376
IS - 6
ER -