Cover Picture: A Concise Total Synthesis of Amphidinin B (Chin. J. Chem. 1/2013)

Authors

  • Dongdong Wu,

    1. Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
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  • Jinlong Wu,

    1. Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
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  • Wei-min Dai

    Corresponding author
    1. Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
    2. Laboratory of Advanced Catalysis and Synthesis, Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China
    • Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
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Abstract

original image

The cover picture shows a concise total synthesis of amphidinin B, a polyketide metabolite isolated from the extracts of cultured marine dinoflagellates Amphidinium sp. (Y-56 strain). By playing a ring-forming trick, selective oxidative cleavage at the two monosubstituted alkene sites was achieved in the presence of the 1,1-disubstituted counterpart. Thus, starting from the triene precursor a ring-closing metathesis (RCM) reaction was performed to form the (12E)- and (12Z)-cycloalkenes. The latter were then subjected to regio- and stereoselective asymmetric dihydroxylation (AD), respectively, to produce the 12,13-diols. Further oxidative cleavage of the diols furnished amphidinin B. More details are discussed in the article by Dai et al. on page 105–110.

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