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

@article{Hanessian2003ApplicationOC,
  title={Application of conformation design in acyclic stereoselection: total synthesis of borrelidin as the crystalline benzene solvate.},
  author={S. Hanessian and Y. Yang and Simon Giroux and Vincent Mascitti and J. Ma and F. Raeppel},
  journal={Journal of the American Chemical Society},
  year={2003},
  volume={125 45},
  pages={
          13784-92
        }
}
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… Expand
Total synthesis of the cytotoxic cyclodepsipeptide (-)-doliculide: the "ester" effect in acyclic 1,3-induction of deoxypropionates.
Convergent synthesis of deoxypropionates.
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