Enantioselective cyclization of chiral butane-1,4-diols to chiral tetrahydrofurans: synthesis of chiral trans-2-(3-methoxy-5-methylsulfonyl-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (L-659,989), a potent PAF-receptor antagonist |
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| Affiliation: | 1. Department of Medical Pharmacology, Faculty of Medicine, Yozgat Bozok University, Yozgat, Turkey;2. Department of Science, Faculty of Education, Afyon Kocatepe University, Afyonkarahisar, Turkey;3. Department of Inorganic Chemistry, Science Institute, Dicle University, Diyarbakır, Turkey;4. Department of Analytical Chemistry, Faculty of Pharmacy, Erzincan Binali Yıldırım University, Erzincan 24002, Turkey;5. Department of Analytical Chemistry, Faculty of Pharmacy, Dicle University, Diyarbakir 21280, Turkey |
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| Abstract: | Acid catalyzed cyclization of (1R,4RS)- and (1S,4RS)-1-(3-methoxy-5-methylsulfonyl-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butane-1,4-diols to the corresponding chiral cis- and trans-tetrahydrofurans proceeds with retention of configuration at C-1. Using this stereo- and regioselective reaction, the two optically active enantiomers of L-659,989, a potent PAF-receptor antagonist, were prepared. |
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