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

Authors:
Dr Kovela Satish, PhD
Dr Kovela Satish, PhD
Indian Institute of Chemical Technology, Hyderabad
Synthetic and medicinal chemistry
Hyderabad, Telangana | India

Org Lett 2018 11 5;20(22):7293-7297. Epub 2018 Nov 5.

Department of Molecular Cell and Developmental Biology and Center for Molecular Biology of RNA , University of California , Santa Cruz , California 95064 , United States.

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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Source
http://pubs.acs.org/doi/10.1021/acs.orglett.8b03228
Publisher Site
http://dx.doi.org/10.1021/acs.orglett.8b03228DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6519444PMC
November 2018
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