title: Collective total synthesis of PPAPs: total synthesis of clusianone via intramolecular cyclopropanation.
abstract: The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- and stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis ofclusianone.
authors: Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
authors: Masahiro
authors: M
authors: Uwamori
authors: Masahisa
authors: M
authors: Nakada
mesh_terms: D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003521:Cyclopropanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C118110:7-epiclusianone; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds; D003521:Cyclopropanes; C030797:cyclopropane