Application of conformation design in acyclic stereoselection: total synthesis of borrelidin as the crystalline benzene solvate.

  title={Application of conformation design in acyclic stereoselection: total synthesis of borrelidin as the crystalline benzene solvate.},
  author={Stephen Hanessian and Yang Yang and Simon Giroux and Vincent Mascitti and Jianguo Ma and Franck Raeppel},
  journal={Journal of the American Chemical Society},
  volume={125 45},
The total synthesis of (-)-borrelidin (treponemycin), a structurally distinct 18-membered macrolide antibiotic, has been achieved. It was isolated as the crystalline benzene solvate, and its structure was confirmed by a single-crystal X-ray analysis. The deoxypropionate subunit consisting of four alternating C-methyl groups with a C(4)-C(10) syn/syn/anti orientation was elaborated by a new method of iterative cuprate additions to acyclic alpha,beta-unsaturated esters relying on two consecutive… 
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