title: Stereoselective total synthesis of garsubellin A.
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.
authors: Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, Tokyo, Japan.
authors: Masahiro
authors: M
authors: Uwamori
authors: Masahisa
authors: M
authors: Nakada
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002795:Choline O-Acetyltransferase; D003521:Cyclopropanes / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D003521:Cyclopropanes; D013729:Terpenes; C106690:garsubellin A; D002795:Choline O-Acetyltransferase