ol7b03456_si_001.pdf (3.45 MB)
Enantioselective Synthesis of Spliceostatin G and Evaluation of Bioactivity of Spliceostatin G and Its Methyl Ester
journal contribution
posted on 2017-12-07, 20:40 authored by Arun K. Ghosh, Guddeti Chandrashekar Reddy, Andrew J. MacRae, Melissa S. JuricaAn 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.