スギウラ マサハル   Sugiura Masaharu
  杉浦 正晴
   所属   崇城大学  薬学部 薬学科
   崇城大学大学院  薬学研究科 薬学専攻
   職種   教授
言語種別 英語
発行・発表の年月 2016/02
形態種別 原著論文
査読 査読有り
標題 Concise Asymmetric Construction of C<inf>2</inf>-symmetric 1,9-Diarylnonanoids Using a Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone
執筆形態 共著
掲載誌名 Chemistry - An Asian Journal
掲載区分国外
巻・号・頁 11,pp.376-379
著者・共著者 Shunsuke Kotani, Shunsuke Kotani, Kosuke Kai, Yasushi Shimoda, Hao Hu, Shen Gao, Masaharu Sugiura, Masamichi Ogasawara, Makoto Nakajima
概要 © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.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.
DOI 10.1002/asia.201501080
ISSN 18614728
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