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Toward the Synthesis of Yuzurimine-Type Alkaloids: Stereoselective Construction of the Heterocyclic Portions of Deoxyyuzurimine and Macrodaphnine.
Hayakawa, Ichiro; Nagatani, Ryosuke; Ikeda, Masaki; Yoo, Dong-Eun; Saito, Keita; Kigoshi, Hideo; Sakakura, Akira.
Affiliation
  • Hayakawa I; Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushima-naka , Kita-ku, Okayama 700-8530 , Japan.
  • Nagatani R; Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushima-naka , Kita-ku, Okayama 700-8530 , Japan.
  • Ikeda M; Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushima-naka , Kita-ku, Okayama 700-8530 , Japan.
  • Yoo DE; Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushima-naka , Kita-ku, Okayama 700-8530 , Japan.
  • Saito K; Department of Chemistry, Graduate School of Pure and Applied Sciences , University of Tsukuba , 1-1-1 Tennodai , Tsukuba 305-8571 , Japan.
  • Kigoshi H; Department of Chemistry, Graduate School of Pure and Applied Sciences , University of Tsukuba , 1-1-1 Tennodai , Tsukuba 305-8571 , Japan.
  • Sakakura A; Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushima-naka , Kita-ku, Okayama 700-8530 , Japan.
Org Lett ; 21(16): 6337-6341, 2019 08 16.
Article in En | MEDLINE | ID: mdl-31361502
ABSTRACT
The heterocyclic portions of yuzurimine-type alkaloids, such as deoxyyuzurimine and macrodaphnine, were synthesized by using a stereoselective hydroboration-oxidation reaction to install the C20 methyl group, the intramolecular Mitsunobu reaction to construct the E-ring portion, and the intramolecular SN2 reaction to construct the F-ring portion as key steps.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2019 Document type: Article Affiliation country: Japón
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2019 Document type: Article Affiliation country: Japón