An efficient synthesis of the C27-C45 fragment of lagunamide A, a cyclodepsipeptide with potent cytotoxic and antimalarial properties

@article{Liu2014AnES,
  title={An efficient synthesis of the C27-C45 fragment of lagunamide A, a cyclodepsipeptide with potent cytotoxic and antimalarial properties},
  author={Hui-ming Liu and Chieh-Yu Chang and Y. Lai and Mei Due Yang and Ching-Yao Chang},
  journal={Tetrahedron-asymmetry},
  year={2014},
  volume={25},
  pages={187-192}
}
An efficient and stereoselective synthesis of the entire C27–C45 moiety of lagunamide A has been achieved from 1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]propan-1-one in six steps with 22% overall yield. The key step in the synthesis is an asymmetric acetal aldol reaction featuring the enantioselective addition of a chiral thiazolidinethione-derived titanium enolate to an acetal to establish the stereochemistry at C39. 

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