Details
| Original language | English |
|---|---|
| Pages (from-to) | 7867-7876 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 53 |
| Issue number | 23 |
| Publication status | Published - 9 Jun 1997 |
| Externally published | Yes |
Abstract
Nucleophilic additions of silyl- and sulfur-stabilized carbanions 5a-e to carbohydrate-derived 2,3-dihydro-4H-pyran-4-ones 4a,b are described. Depending on the combination of substituents attached to the C1-anion, either 1,2- or 1,4-adducts are preferentially formed. Coupling of vinyl cuprate derived from 16 with enone 4a stereoselectively afforded pyranone 17 which is a potential precursor for thromboxane analogues.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Organic Chemistry
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In: Tetrahedron, Vol. 53, No. 23, 09.06.1997, p. 7867-7876.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Addition of C-nucleophiles to carbohydrate-derived 2,3-dihydro-4H-pyran-4-ones
T2 - A new entry to thriomboxane analogues
AU - Kirschning, Andreas
AU - Harders, Jan
N1 - Funding information: Acknowledgement: We thank Dr. W. Skuballa (Schering AG, Berlin) for helpful discussions. Financial support by the Deutsche Forschungsgemeinschaft (grant Ki 397/4-l) and the Fonds der Chemischen Industrie is gratefully acknowledged.
PY - 1997/6/9
Y1 - 1997/6/9
N2 - Nucleophilic additions of silyl- and sulfur-stabilized carbanions 5a-e to carbohydrate-derived 2,3-dihydro-4H-pyran-4-ones 4a,b are described. Depending on the combination of substituents attached to the C1-anion, either 1,2- or 1,4-adducts are preferentially formed. Coupling of vinyl cuprate derived from 16 with enone 4a stereoselectively afforded pyranone 17 which is a potential precursor for thromboxane analogues.
AB - Nucleophilic additions of silyl- and sulfur-stabilized carbanions 5a-e to carbohydrate-derived 2,3-dihydro-4H-pyran-4-ones 4a,b are described. Depending on the combination of substituents attached to the C1-anion, either 1,2- or 1,4-adducts are preferentially formed. Coupling of vinyl cuprate derived from 16 with enone 4a stereoselectively afforded pyranone 17 which is a potential precursor for thromboxane analogues.
UR - http://www.scopus.com/inward/record.url?scp=0030916615&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(97)00475-4
DO - 10.1016/S0040-4020(97)00475-4
M3 - Article
AN - SCOPUS:0030916615
VL - 53
SP - 7867
EP - 7876
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 23
ER -