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Keywords:

  • amphidinin B;
  • cycloalkene;
  • dihydroxylation;
  • oxidative cleavage;
  • total synthesis
Thumbnail image of graphical abstract

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.