SYNTHETIC STUDIES TOWARD HENNOXAZOLE A. USE OF A SELECTIVE BISOXAZOLE ALKYLATION AS THE KEY FRAGMENT COUPLING

@article{Smith2002SYNTHETICST,
  title={SYNTHETIC STUDIES TOWARD HENNOXAZOLE A. USE OF A SELECTIVE BISOXAZOLE ALKYLATION AS THE KEY FRAGMENT COUPLING},
  author={Thomas E. Smith and Emily P. Balskus},
  journal={Heterocycles},
  year={2002},
  volume={57},
  pages={1219-1225}
}
A model system for side chain fragment coupling to the core of hennoxazole A is investigated. Lateral metallation of a C 1 3 -TBS-protected bisoxazole, using lithium diethylamide, allows for selective and efficient alkylation at C 1 5 . 

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References

SHOWING 1-4 OF 4 REFERENCES
A total synthesis of the unique tris-oxazole macrolide ulapualide A produced by the marine nudibranch Hexabranchus sanguineus
A total synthesis of ulapualide A (1), whose relative stereochemistry was assigned on the basis of an earlier molecular mechanics study of its hypothetical metal chelated complex 9, is described. The
Total Synthesis of Nominal Diazonamides—Part 1: Convergent Preparation of the Structure Proposed for (−)-Diazonamide A
Representative procedure for the preparation of 7: A solution of lithium hexamethyldisilazide in THF (1, 0.20 mL, 0.20 mmol) was added dropwise to a solution of 1 (0.038 g; 0.20 mmol) in THF (0.5 mL)
Angew
  • Chem. Int. Ed.,
  • 2001
For a review of classical methods of oxazole synthesis see : ( b ) I . J . Turchi , ‘ Oxazoles ’ in ‘ Heterocyclic Compounds
  • 1986