Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide

HIGHLIGHTS

• What: Inspired by the biosynthesis of the cephalotane natural products, the authors report here a single-atom insertion into the framework of the benzenoid subfamily, providing access to the troponoid congeners - representing the reverse of the proposed biosynthesis (i.e., a contra-biosynthesis approach). The authors report the realization of the benzenoid-to-troponoid conversion of the cephalotanes, culminating in a two-step synthesis of harringtonolide from cephanolide A. Notably, the success of the studies was guided by valuable insights gained through computational analysis of the key ring expansion reaction. The X-ray crystallographic coordinates for structures . . .
  

   

  

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