Enantioselective Synthesis of Spliceostatin G and
Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester

Jurica, Melissa S.

Enantioselective Synthesis of Spliceostatin G and Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester

Posted on 2017-12-07 - 20:40

An enantioselective total synthesis of spliceostatin G has been accomplished. The synthesis involved a Suzuki cross-coupling reaction as a key step. The functionalized tetrahydropyran ring was constructed from commercially available optically active tri-O-acetyl-d-glucal. Other key reactions include a highly stereoselective Claisen rearrangement, a Cu(I)-mediated 1,4 addition of MeLi to install the C8 methyl group, and a reductive amination to incorporate the C10 amine functionality of spliceostatin G. Biological evaluation of synthetic spliceostatin G and its methyl ester revealed that it does not inhibit splicing in vitro.

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Ghosh, Arun K.; Reddy, Guddeti Chandrashekar; MacRae, Andrew J.; Jurica, Melissa S. (2017). Enantioselective Synthesis of Spliceostatin G and Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b03456

https://doi.org/10.1021/acs.orglett.7b03456

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