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Formal Synthesis of (±)-Morphine

Authors

  • Jing Li,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Guo-Liang Liu,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Xian-He Zhao,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Ji-Yuan Du,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Hu Qu,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Wen-Dao Chu,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Ming Ding,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Cong-Yang Jin,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Meng-Xue Wei,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
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  • Prof. Dr. Chun-An Fan

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516
    2. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Lu, Beijing 100191 (China)
    • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000 (China), Fax: (+86) 931-8915516

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Abstract

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The pain ends here: A novel synthetic strategy for the construction of (±)-morphine rings B and E was developed, in which SmI2-promoted reductive coupling/desulfurization and tandem alcoholysis/oxa-Michael addition featured as the key steps for the assembly of the C9[BOND]C14 and C5[BOND]O bonds, respectively. Asymmetric tandem alcoholysis/oxa-Michael addition was also feasible for the enantiocontrolled synthesis of morphine.

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