title: Concise Asymmetric Construction of C2 -symmetric 1,9-Diarylnonanoids Using a Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone.
abstract: By using a phosphine oxide-catalyzed enantioselective double aldol reaction, we achieved the concise construction of C2 -symmetric 1,9-diarylnonanoids, enabling the synthesis of (-)-ericanone from p-hydroxybenzaldehyde in 6 steps with 65 % overall yield. The enantioselective double aldol reaction is useful for establishing C2 -symmetric 1,9-diaryl-3,7-dihydroxy-5-nonanones with a single operation. Furthermore, the use of o-nosyl-protected p-hydroxybenzaldehyde and a 4,4'-disubstituted BINAP dioxide catalyst dramatically improved the reactivity and selectivity in the double aldol reaction, enabling the total synthesis of (-)-ericanone with high yield and with excellent enantiopurity.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan. skotani@gpo.kumamoto-u.ac.jp.|Priority Organization for Innovation and Excellence, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan. skotani@gpo.kumamoto-u.ac.jp.
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Kotani
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Kai
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan.
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Shimoda
authors.affiliation: Catalysis Research Center and Graduate School of Life Science, Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, 001-0021, Japan.
authors.forename: Hao
authors.initials: H
authors.lastname: Hu
authors.affiliation: Catalysis Research Center and Graduate School of Life Science, Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, 001-0021, Japan.
authors.forename: Shen
authors.initials: S
authors.lastname: Gao
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan.
authors.forename: Masaharu
authors.initials: M
authors.lastname: Sugiura
authors.affiliation: Catalysis Research Center and Graduate School of Life Science, Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, 001-0021, Japan.
authors.forename: Masamichi
authors.initials: M
authors.lastname: Ogasawara
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto, 862-0973, Japan. nakajima@gpo.kumamoto-u.ac.jp.
authors.forename: Makoto
authors.initials: M
authors.lastname: Nakajima
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D009281:Naphthalenes / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; C406943:BINAP, 2-naphthol; D001547:Benzaldehydes; D006841:Hydrocarbons, Aromatic; D009281:Naphthalenes; D010087:Oxides; D010720:Phosphines; C116609:3-hydroxybutanal; C044646:phosphine; C011483:4-hydroxybenzaldehyde; D012825:Silicon
keywords: 1,9-diarylnonanoids; C2-symmetry; aldol reaction; hypervalent silicon complex; phosphine oxides