%0 Journal Article %A Ghosh, Arun K. %A Reddy, Guddeti Chandrashekar %A MacRae, Andrew J. %A Jurica, Melissa S. %D 2017 %T Enantioselective Synthesis of Spliceostatin G and Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester %U https://acs.figshare.com/articles/journal_contribution/Enantioselective_Synthesis_of_Spliceostatin_G_and_Evaluation_of_Bioactivity_of_Spliceostatin_G_and_Its_Methyl_Ester/5682679 %R 10.1021/acs.orglett.7b03456.s001 %2 https://ndownloader.figshare.com/files/9938221 %K Suzuki cross-coupling reaction %K C 10 amine functionality %K Spliceostatin G %K functionalized tetrahydropyran ring %K stereoselective Claisen rearrangement %K synthesis %K C 8 methyl group %K spliceostatin G %X 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. %I ACS Publications