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Toward the Total Synthesis of Haliclonin A: Construction of a Tricyclic Substructure

Authors

  • Shi-Peng Luo,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China), Fax: (+86) 592-2186400
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  • Lian-Dong Guo,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China), Fax: (+86) 592-2186400
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  • Long-Hui Gao,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China), Fax: (+86) 592-2186400
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  • Shuang Li,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China), Fax: (+86) 592-2186400
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  • Prof. Dr. Pei-Qiang Huang

    Corresponding author
    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China), Fax: (+86) 592-2186400
    2. State Key Laboratory of Bioorganic and Natural Products Chemistry, 345 Ling-Ling Road, Shanghai 200032 (P.R. China)
    • Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China), Fax: (+86) 592-2186400
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Abstract

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Three keys to success: A concise method for the construction of a tricyclic substructure (2) of haliclonin A (1) in racemic form is described (see figure). This synthesis features a new Pd-mediated chemoselective carbonyl–enone coupling reaction, an organocatalytic reaction, and a ring-closing metathesis reaction for the construction of the macrocyclic ring as key steps.

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