Synthesis and in vitro antitumour activity of crassalactone D, its stereoisomers and novel cinnamic ester derivatives.

@article{Kovacevic2017SynthesisAI,
  title={Synthesis and in vitro antitumour activity of crassalactone D, its stereoisomers and novel cinnamic ester derivatives.},
  author={Ivana Kostic Kovacevic and Mirjana M Popsavin and Goran Benedekovi{\'c} and Jelena Kesi{\'c} and Vesna Kojic and Dimitar S. Jakimov and Tatjana Srdiċ-Rajiċ and Gordana M. Bogdanovi{\'c} and Vladimir Divjakovi{\'c} and Velimir Popsavin},
  journal={European journal of medicinal chemistry},
  year={2017},
  volume={134},
  pages={
          293-303
        }
}
Naturally occurring styryl lactone, crassalactone D (1), unnatural 4-epi-crassalactone D (2), and the corresponding 7-epimers (3 and 4) have been synthesized starting from d-glucose. The key step of the synthesis is a new one-pot sequence that commenced with a Z-selective Wittig olefination of suitably functionalized sugar lactols with a stabilized ylide, (methoxycarbonylmethylene)-triphenylphosphorane, in dry methanol, to afford 1 or 3, in the mixtures with the corresponding 4-epimers (2 or 4… CONTINUE READING