Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 1958-1972 |
| Seitenumfang | 15 |
| Fachzeitschrift | European Journal of Organic Chemistry |
| Jahrgang | 2003 |
| Ausgabenummer | 10 |
| Publikationsstatus | Veröffentlicht - 5 Mai 2003 |
| Extern publiziert | Ja |
Abstract
A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: European Journal of Organic Chemistry, Jahrgang 2003, Nr. 10, 05.05.2003, S. 1958-1972.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Stereoselective Synthesis ofmyo-,neo-,L-chiro,D-chiro,allo-,scyllo-, andepi-Inositol Systems via Conduritols Prepared fromp-Benzoquinone
AU - Podeschwa, Michael
AU - Plettenburg, Oliver
AU - Vom Brocke, Jochen
AU - Block, Oliver
AU - Adelt, Stephan
AU - Altenbach, Hans Josef
PY - 2003/5/5
Y1 - 2003/5/5
N2 - A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity.
AB - A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity.
KW - Asymmetric synthesis
KW - Chiral resolution
KW - HPIC-IPAD
KW - Natural products
UR - http://www.scopus.com/inward/record.url?scp=0038181194&partnerID=8YFLogxK
U2 - 10.1002/ejoc.200200572
DO - 10.1002/ejoc.200200572
M3 - Article
AN - SCOPUS:0038181194
VL - 2003
SP - 1958
EP - 1972
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 10
ER -