Asymmetric synthesis via acetal templates. 15. The preparation of enantiomerically pure mevinolin analogs |
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| Institution: | 1. Department of Chemistry, Stanford University, Stanford, California 94305 USA;2. Department of Medicinal Chemistry, Smith Kline and French Laboratories, P. O. Box 1539, King of Prussia, Pennsylvania 19406-0939 USA;1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation;1. State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan University, and Collaborative Innovation Center for Biotherapy, Chengdu, Sichuan 610041, PR China;2. School of Chemical Engineering, Sichuan University, Chengdu, Sichuan 610065, PR China;3. Key Laboratory of Drug Targeting and Drug Delivery System, Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan 610041, PR China |
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| Abstract: | An efficient asymmetric synthesis of the hydroxylactone moiety of mevinolin 1 is described. The key step is the TiCl4-catalyzed coupling reaction of acetals 3a and 3b derived from (R)-1,3-butanediol with 1,3-bis(trimethylsilyloxy)-1-methoxybuta-1,3-diene 4 to give the δ-alkoxy-β-keto ester 5. |
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