| A Flexible Approach to the γ－Amino－β－hydroxy Acid Moiety of Hapalosin |
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| 引用本文： | 黄培强,吴天俊,叶剑良.A Flexible Approach to the γ－Amino－β－hydroxy Acid Moiety of Hapalosin[J].中国化学,2003,21(7):723-726. |
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| 作者姓名： | 黄培强 吴天俊 叶剑良 |
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| 作者单位： | DepartmentofChemistry,XiamenUniversity,Xiamen,Fujian361005,China |
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| 基金项目： | Project supported by the National Science Foundation for Distinguished Young Investigators,the National Natural Science Foundation of China and the Fund for doctoral sites of the Ministry of Education. |
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| 摘 要： | A flexible approach to ethyl (3R,4S)-N-Boc-4-amino-3-hydroxy-5-phenylpentanoate (N-Boc-AHPPA-OEt), the γ-amino-β-hydroxy acid moiety of hapalosin is described. The synthetic method features a ring-opening ethanolysis of an activated N-Boc-lactam, which is obtained via a diastereoselective reductive-alkylation of (R)-malimide derivative. The flexibility of the method resides in the introduction of the alkyl side chain by Grignard reagent addition.
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| 关 键 词： | γ－氨基－β－羟基酸 合成方法 开链反应 乙醇分解 乙烷基（3R 4S）－N－Boc－4－氨基－3－羟基－5－苯基戊酸 软管藻素 蓝绿藻提取物 多药耐药性 |
A Flexible Approach to the γ‐Amino‐β‐hydroxy Acid Moiety of Hapalosin |
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| HUANG,Pei-Qiang WU,Tian-Jun YE,Jian-Liang.A Flexible Approach to the γ‐Amino‐β‐hydroxy Acid Moiety of Hapalosin[J].Chinese Journal of Chemistry,2003,21(7):723-726. |
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| Authors: | HUANG Pei-Qiang WU Tian-Jun YE Jian-Liang |
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| Institution: | HUANG,Pei-Qiang WU,Tian-Jun YE,Jian-Liang
Department of Chemistry,Xiamen University,Xiamen,Fujian 361005,China |
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| Abstract: | A flexible approach to ethyl (3R.4S)‐N‐Boc‐4‐amino‐3‐hydroxy‐S‐phenylpentanoate (N‐Boc‐AHPPA‐OEt), the γ‐aminoβ‐hydroxy add moiety of hapalosin is described. The synthetic method features a ring‐opening ethanolysis of an activated N‐Boc‐lactam, which is obtained via a diastereoselective reductive‐alkylation of (R)‐malimide derivative. The flexibility of the method resides in the introduction of the alkyl side chain by Grignard reagent addition. Project supported by the National Science Foundation for Distinguished Young Investigators, the National Natural Science Foundation of China and the Fund for doctoral sites of the Ministry of Education. |
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| Keywords: | (R)-malic acid hapalosin anti-AHPPA asymmet-ric synthesis reductive alkylation |
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