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Stereoselective total synthesis of garsubellin A
Masahiro Uwamori1, Masahisa Nakada
1Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, Tokyo, Japan.
Abstract:
The stereoselective total synthesis of garsubellin A is described. The total synthesis was achieved through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence: intramolecular cyclopropanation, formation of a germinal dimethyl group, and regioselective ring opening of cyclopropane. To complete the total synthesis of garsubellin A, chemo- and stereoselective hydrogenation to generate the C8 stereogenic center is followed by the formation of the fused tetrahydrofuran ring by a regioselective epoxide-opening reaction with C3 ketone, and finally cross metathesis to construct two prenyl groups.
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