Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthesis of an ester side chain |
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| Authors: | Xue Zhi Zhao Lei Peng Xue Qiang Li Yan Xing Jia |
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| Institution: | Department of Chemistry & State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China |
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| Abstract: | The stereocontrolled synthesis of the C1-C8 portion, the ester side chain of the HIV-1 protease inhibitive didemnaketals from the ascidian Didemnum sp., has been carried out through 15 steps starting from (S)-carvone as the chiral template. This approach involved the diastereoselective construction of three conjoint chiral centers by intramolecular chiral inducement, and generation of allylic alcohol intermediate through a key Grob fragmentation reaction. |
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| Keywords: | Ester side chain HIV-1 protease Intramolecular chiral inducement Grob fragmentation reaction |
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