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Enantioselective Synthesis of a Cyclopropane Derivative of Spliceostatin A and Evaluation of Bioactivity
- Ghosh, Arun K;
- Reddy, Guddeti Chandrashekar;
- Kovela, Satish;
- Relitti, Nicola;
- Urabe, Veronica K;
- Prichard, Beth E;
- Jurica, Melissa S
Published Web Location
https://doi.org/10.1021/acs.orglett.8b03228Abstract
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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