title: Total synthesis of (-)-bucidarasin a starting from an original chiral building block.
abstract: The highly stereoselective total synthesis of (-)-bucidarasin A, which also elucidated the absolute structure of its natural form, is described. The total synthesis features effective use of the original chiral building block prepared by us and a series of highly stereoselective reactions, i.e., hydroxy-directed hydrogenation, [4 + 2] cycloaddition of a sterically hindered dienophile, reduction of ketones, formation of the C9 side-chain diene, and formation of the THF moiety bearing two acetyloxy groups.
authors.affiliation: Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University 3-4-1 Ohkubo , Shinjuku-ku, Tokyo 169-8555, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Usui
authors.forename: Misaki
authors.initials: M
authors.lastname: Kanbe
authors.forename: And Masahisa
authors.initials: AM
authors.lastname: Nakada
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006865:Hydrogenation; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D004224:Diterpenes; D007659:Ketones; C456402:bucidarasin A