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Evidence for a Trianion Intermediate in the Metalation of 4-Hydroxy-6,7-dimethoxy-8-methyl-2-naphtoic Acid. Methodology and Application to Racemic 5,5'-Dideisopropyl-5,5'-dialkylapogossypol Derivatives
- Source :
- Journal of Organic Chemistry, Journal of Organic Chemistry, American Chemical Society, 2011, 76 (2), pp.601-608. ⟨10.1021/jo102147s⟩
- Publication Year :
- 2011
- Publisher :
- HAL CCSD, 2011.
-
Abstract
- The metalation of 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid (8) affording trianion 6 is presented and applied to the regioselective efficient construction of a series of 5,5'-didesisopropyl-5,5'-dialkylapogossypol derivatives 3 that are potent pan-active inhibitors of antiapoptotic Bcl-2 family proteins.
- Subjects :
- Anions
Magnetic Resonance Spectroscopy
Stereochemistry
Metalation
Apoptosis
Naphthalenes
010402 general chemistry
01 natural sciences
Mice
Organic chemistry
Animals
ComputingMilieux_MISCELLANEOUS
Molecular Structure
010405 organic chemistry
Chemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Organic Chemistry
Gossypol
Regioselectivity
Stereoisomerism
0104 chemical sciences
Antiapoptotic Agent
Proto-Oncogene Proteins c-bcl-2
Metals
Lithium Compounds
Naphthoic acid
Subjects
Details
- Language :
- English
- ISSN :
- 00223263 and 15206904
- Database :
- OpenAIRE
- Journal :
- Journal of Organic Chemistry, Journal of Organic Chemistry, American Chemical Society, 2011, 76 (2), pp.601-608. ⟨10.1021/jo102147s⟩
- Accession number :
- edsair.doi.dedup.....5caa89ee5722299c505786d7d363d080