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- W2950795506 abstract "Retinoids 1−5 have been identified as potent RXR agonists for evaluation in the treatment of non-insulin-dependent (type II) diabetes mellitus (NIDDM). Highly convergent syntheses of 1−5 have been developed. The core tetrahydronaphthalene 7, employed in the synthesis of 1 and 2, was prepared in 98% yield using an AlCl3-catalyzed (0.03 equiv) Friedel−Crafts alkylation of toluene with 2,5-dichloro-2,5-dimethylhexane 6. A nitromethane-mediated Fridel−Crafts acylation of 7 with chloromethylnicotinate 9 was developed to prepare ketone 10 in 68% yield. Chelate-controlled addition of MeMgCl to 10 followed by dehydration afforded olefin 11 in 65% yield. Cyclopropanation of 11 with trimethylsulfoxonium ylide, followed by saponification, completed a five-step synthesis of 1 in 33% yield. FeCl3-catalyzed (0.05 equiv) Friedel−Crafts acylation of 7 with chloromethylterephthalate 14 afforded ketone 15 in 81% yield. Saponification of 15 and reaction with 50% aqueous NH2OH in AcOH afforded a 9:1 mixture of cis and trans ..." @default.
- W2950795506 created "2019-06-27" @default.
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- W2950795506 date "2010-05-23" @default.
- W2950795506 modified "2023-09-25" @default.
- W2950795506 title "ChemInform Abstract: Synthesis of Novel Retinoid X Receptor-Selective Retinoids." @default.
- W2950795506 cites W1999989693 @default.
- W2950795506 doi "https://doi.org/10.1002/chin.200151118" @default.
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