The conjugate addition–Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands
Mazhar Iqbal
1
,
Patricia Duffy
2
,
Paul Evans
2
,
George Cloughley
3
,
Allan Bernard
3
,
Agustí Lledó
4
,
Xavier Verdaguer
4
,
A. Riera
4
Publication type: Journal Article
Publication date: 2008-11-04
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
DOI:
10.1039/b814619e
PubMed ID:
19039376
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
5-Alkylidenecyclopent-2-enones 15a-q may be prepared via a conjugate addition-Peterson olefination sequence, best achieved in one-pot, using exo-2-trimethylsilyl-3a,4,7,7a-tetrahydro-4,7-methanoinden-1-one 12, followed by a retro-Diels-Alder reaction. The geometry of the exocyclic alkene may be controlled according to the use of organometallic species in the conjugate addition step; organocuprate reagents are found to selectively lead to the formation of E-exocyclic alkene adducts, whereas Grignard reagents favour the formation of Z-alkenyl isomers. The use of enantiomerically enriched 12, accessed from an asymmetric Pauson-Khand reaction, affords the corresponding enantioenriched 5-alkylidenecyclopent-2-enones and this approach is exemplified by the short, stereoselective total syntheses of two cyclopentenone phytoprostanes 51 and 13,14-dehydrophytoprostane J1 65. The ability of this family of synthetic compounds to activate the peroxisome proliferator activated receptor-gamma is reported.
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Iqbal M. et al. The conjugate addition–Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands // Organic and Biomolecular Chemistry. 2008. Vol. 6. No. 24. p. 4649.
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Iqbal M., Duffy P., Evans P., Cloughley G., Bernard A., Lledó A., Verdaguer X., Riera A. The conjugate addition–Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands // Organic and Biomolecular Chemistry. 2008. Vol. 6. No. 24. p. 4649.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/b814619e
UR - https://doi.org/10.1039/b814619e
TI - The conjugate addition–Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands
T2 - Organic and Biomolecular Chemistry
AU - Iqbal, Mazhar
AU - Duffy, Patricia
AU - Evans, Paul
AU - Cloughley, George
AU - Bernard, Allan
AU - Lledó, Agustí
AU - Verdaguer, Xavier
AU - Riera, A.
PY - 2008
DA - 2008/11/04
PB - Royal Society of Chemistry (RSC)
SP - 4649
IS - 24
VL - 6
PMID - 19039376
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
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@article{2008_Iqbal,
author = {Mazhar Iqbal and Patricia Duffy and Paul Evans and George Cloughley and Allan Bernard and Agustí Lledó and Xavier Verdaguer and A. Riera},
title = {The conjugate addition–Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands},
journal = {Organic and Biomolecular Chemistry},
year = {2008},
volume = {6},
publisher = {Royal Society of Chemistry (RSC)},
month = {nov},
url = {https://doi.org/10.1039/b814619e},
number = {24},
pages = {4649},
doi = {10.1039/b814619e}
}
Cite this
MLA
Copy
Iqbal, Mazhar, et al. “The conjugate addition–Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands.” Organic and Biomolecular Chemistry, vol. 6, no. 24, Nov. 2008, p. 4649. https://doi.org/10.1039/b814619e.