Parallel synthesis of individual shikimic acid-like molecules using a mixture-operation strategy and ring-closing enyne metathesis |
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| Authors: | Fang Hu Zhu-Jun Yao |
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| Affiliation: | a State Key Laboratory of Bioorganic and Natural Product Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China
b Department of Analysis Chemistry, Hunan Traditional Chinese Medicine University, 113 Middle Shaoshan Road, Changsha, Hunan 410007, China |
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| Abstract: | Three new diastereomeric shikimic acid analogues (4-amino-3,5-dihydroxyl-cyclohex-1-en-carboxylic acids, 16) bearing a C-4 amino group were synthesized in parallel by a mixture-operation protocol. Ring-closing enyne metathesis (RCEYM) under ethylene atmosphere was successfully employed to construct the desired carbocycles in high efficiency. The absolute configurations of each final product were confirmed by the 1D and 2D NMR techniques. |
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| Keywords: | Shikimic acid Carbocycle Ring-closing enyne metathesis Stereochemistry Parallel synthesis |
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