| Synthesis of 1-[6-Fluoro-(2S)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2- ethanediol and 1-[6-Fluoro-(2R)-3H,4H-dihydro-2H-2-chromenyl]- (1R)-1,2-ethanediol |
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| 引用本文： | YU,An-Guang WANG,Nai-Xing ZHANG,Jun-Ping YANG,Yun-Xu WANG,Wu-Wei SHENG,Rui-Long. Synthesis of 1-[6-Fluoro-(2S)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2- ethanediol and 1-[6-Fluoro-(2R)-3H,4H-dihydro-2H-2-chromenyl]- (1R)-1,2-ethanediol[J]. 有机化学, 2004, 24(Z1): 31-32 |
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| 作者姓名： | YU An-Guang WANG Nai-Xing ZHANG Jun-Ping YANG Yun-Xu WANG Wu-Wei SHENG Rui-Long |
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| 作者单位： | YU,An-Guang（Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101） WANG,Nai-Xing（Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101） ZHANG,Jun-Ping（Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101） YANG,Yun-Xu（Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101） WANG,Wu-Wei（Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101） SHENG,Rui-Long（Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100101） |
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| 基金项目： | 国家自然科学基金，国家高技术研究发展计划(863计划) |
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| 摘 要： | Benzopyran compounds possess diverse pharmacological properties such as β-blockade, anticonvulsant and antimicrobial.[1,2] Our interest has been focused on the synthesis of 1-[6-Fluoro-2S]-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2-ethanediol (6) and 1-[6-fluoro-(2R)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2-ethanediol (7) which are particularly convenient precursor to (S,R,R,R)-NE (8). 8 containing four asymmetrical carbon atoms was reported to be the most active isomer.[3] Chandrasekhar[4] has reported on the synthesis of 8. The key step to synthesize this compound is to obtain the chiral chromanone 6 and 7. 6 was accomplished in 8 steps by the Clasien rearrangement and a one-pot Sharpless asymmetric epoxidation, but the compound 7 was accomplished in 10 steps. Johannes[5] used Zr-catalytic kinetic resolution of allylic ethers and Mo-catalyzed chromene formation to synthesize 8 in 14 steps. However both of the methods request many synthetic steps and expensive reagents.
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Synthesis of 1-[6-Fluoro-(2S)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2- ethanediol and 1-[6-Fluoro-(2R)-3H,4H-dihydro-2H-2-chromenyl]- (1R)-1,2-ethanediol |
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| YU,An-Guang,WANG,Nai-Xing,ZHANG,Jun-Ping,YANG,Yun-Xu,WANG,Wu-Wei,SHENG,Rui-Long. Synthesis of 1-[6-Fluoro-(2S)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2- ethanediol and 1-[6-Fluoro-(2R)-3H,4H-dihydro-2H-2-chromenyl]- (1R)-1,2-ethanediol[J]. Chinese Journal of Organic Chemistry, 2004, 24(Z1): 31-32 |
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| Authors: | YU An-Guang WANG Nai-Xing ZHANG Jun-Ping YANG Yun-Xu WANG Wu-Wei SHENG Rui-Long |
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| Abstract: | Benzopyran compounds possess diverse pharmacological properties such as β-blockade, anticonvulsant and antimicrobial.[1,2] Our interest has been focused on the synthesis of 1-[6-Fluoro-2S]-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2-ethanediol (6) and 1-[6-fluoro-(2R)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2-ethanediol (7) which are particularly convenient precursor to (S,R,R,R)-NE (8). 8 containing four asymmetrical carbon atoms was reported to be the most active isomer.[3] Chandrasekhar[4] has reported on the synthesis of 8. The key step to synthesize this compound is to obtain the chiral chromanone 6 and 7. 6 was accomplished in 8 steps by the Clasien rearrangement and a one-pot Sharpless asymmetric epoxidation, but the compound 7 was accomplished in 10 steps. Johannes[5] used Zr-catalytic kinetic resolution of allylic ethers and Mo-catalyzed chromene formation to synthesize 8 in 14 steps. However both of the methods request many synthetic steps and expensive reagents. |
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