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Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid |
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| Authors: | Bhaskar C Das George W Kabalka |
| Institution: | a Department of Nuclear Medicine, Albert Einstein College of Medicine, Bronx, NY 10461, USA b Department of Developmental and Molecular Biology, Albert Einstein College of Medicine, Bronx, NY 10461, USA c Albert Einstein College Cancer Center, Albert Einstein College of Medicine, Bronx, NY 10461, USA d Departments of Chemistry and Radiology, The University of Tennessee, Knoxville, TN,37996-1600, USA |
| Abstract: | (E)-4-((3-Ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid, 6, was synthesized in 87% starting from β-cyclocitral. The target compound 6 was synthesized starting from 1 via a Grignard reaction to form alcohol 2. Compound 2 was converted to Wittig salt 3 by treatment with aldehyde 4 in butyllithium and hexane at −78 °C to form ester 5. Ester 5 was saponified and, following acidification, acid 6 was isolated as white solid yield 87%. |
| Keywords: | Retinoids Peptidomimetics 1 4 Diene and Wittig reaction |
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