Details
| Original language | English |
|---|---|
| Pages (from-to) | 1958-1972 |
| Number of pages | 15 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2003 |
| Issue number | 10 |
| Publication status | Published - 5 May 2003 |
| Externally published | Yes |
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.
Keywords
- Asymmetric synthesis, Chiral resolution, HPIC-IPAD, Natural products
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2003, No. 10, 05.05.2003, p. 1958-1972.
Research output: Contribution to journal › Article › Research › 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 -