title: Total synthesis of (-)-FR182877 through tandem IMDA-IMHDA reactions and stereoselective transition-metal-mediated transformations.
abstract: Intelligent design: The total synthesis of the cytotoxic (-)-FR182877 relies on 1) tandem Diels-Alder reactions to close rings A-D (see scheme), 2) a palladium-mediated 7-exo-trig reaction, and 3) an iridium-mediated isomerization followed by epimerization and stereoselective reduction.
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: Natsumi
authors.initials: N
authors.lastname: Tanaka
authors.forename: Takahiro
authors.initials: T
authors.lastname: Suzuki
authors.forename: Takehiko
authors.initials: T
authors.lastname: Matsumura
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Hosoya
authors.forename: Masahisa
authors.initials: M
authors.lastname: Nakada
mesh_terms: D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D007495:Iridium / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C408303:FR 182877; D006576:Heterocyclic Compounds, 4 or More Rings; D008670:Metals; D011083:Polycyclic Compounds; D020005:Propanols; C006463:allyl alcohol; D007495:Iridium; D010165:Palladium