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Open Access Publications from the University of California

Enantioselective Synthesis of a Cyclopropane Derivative of Spliceostatin A and Evaluation of Bioactivity.

  • Author(s): Ghosh, Arun K
  • Reddy, Guddeti Chandrashekar
  • Kovela, Satish
  • Relitti, Nicola
  • Urabe, Veronica K
  • Prichard, Beth E
  • Jurica, Melissa S
  • et al.

Spliceostatin A is a potent inhibitor of spliceosomes and exhibits excellent anticancer activity against multiple human cancer cell lines. We describe here the design and synthesis of a stable cyclopropane derivative of spliceostatin A. The synthesis involved a cross-metathesis or a Suzuki cross-coupling reaction as the key step. The functionalized epoxy alcohol ring was constructed from commercially available optically active tri- O-acetyl-d-glucal. The biological properties of the cyclopropyl derivative revealed that it is active in human cells and inhibits splicing in vitro comparable to spliceostatin A.

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