Hiromi Fukuoka

Publications (2)10.31 Total impact

• Source

  Available from: 217.219.214.30

  Article: Catalytic asymmetric allylation of 3,4-dihydroisoquinolines and its application to the synthesis of isoquinoline alkaloids.

  Michiko Miyazaki, Nami Ando, Keita Sugai, Yuki Seito, Hiromi Fukuoka, Takuya Kanemitsu, Kazuhiro Nagata, Yuki Odanaka, Kazuo T Nakamura, Takashi Itoh
  [show abstract] [hide abstract]
  ABSTRACT: A catalytic asymmetric allylation of 3,4-dihydroisoquinoline was carried out with allyltrimethoxylsilane-Cu as the nucleophile in the presence of DTBM-SEGPHOS as the chiral ligand to afford corresponding chiral 1-allyltetrahydroisoquinoline derivatives in good yield and stereoselectivity. The allyl adduct thus obtained was applied to the synthesis of several isoquinoline alkaloids such as crispine A and homolaudanosine. The reaction was further used for the synthesis of the isoquinoline moiety of schulzeine A.
  The Journal of Organic Chemistry 01/2011; 76(2):534-42. · 4.45 Impact Factor
• Article: Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step.

  Takashi Itoh, Michiko Miyazaki, Hiromi Fukuoka, Kazuhiro Nagata, Akio Ohsawa
  [show abstract] [hide abstract]
  ABSTRACT: [reaction: see text] Catalytic asymmetric allylation of 3,4-dihydro-6,7-dimethoxyisoquinoline was carried out using allyltrimethoxysilane in the presence of Cu(I) and tol-BINAP. The allyl adduct thus obtained was transformed to a chiral synthetic intermediate for (-)-emetine in good yield. The procedure was applied to the total synthesis of ent-emetine.
  Organic Letters 04/2006; 8(7):1295-7. · 5.86 Impact Factor