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【结 构 式】 
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【药物名称】CTC-8 【化学名称】(-)-4(S)-[tert-Butyl(dimethyl)silyloxy]-2-cyclopenten-1-one 【CA登记号】61305-36-0 【 分 子 式 】C11H20O2Si 【 分 子 量 】212.36685 |
【开发单位】Charterhouse Therapeutics (Originator) 【药理作用】Anti-Herpes Virus Drugs, ANTIINFECTIVE THERAPY, Antiviral Drugs, NF-kappaB (NFKB) Activation Inhibitors |
合成路线1
Enantioselective enzyme-catalyzed transesterification of the tricyclic diol (I) with vinyl acetate (II) provides the chiral monoacetate (III). After protection of the free hydroxyl group of (III) as the tert-butyldimethylsilyl ether (IV), alkaline hydrolysis of the acetate ester group yields alcohol (V), which is then oxidized to the corresponding ketone (VI) by means of pyridinium dichromate. Finally, thermal retro-Diels-Alder reaction of (VI) under diminished pressure furnishes the target cyclopentenone derivative.
| 【1】 Liu, Z.-Y.; He, L.; Zheng, H.; Highly enantioselective synthesis of (+) and (-)endo- tricyclo [5.2.1.02,6]deca-4,8-dien-3-one and (-)-4-t-butyldimethylsilyloxy-cyclopentenone by enzyme-catalyzed acetylation. Tetrahedron Asymmetry 1993, 4, 11, 2277. |