Your browser doesn't support javascript.
loading
Progress toward the Total Synthesis of Goniodomin A: Stereocontrolled, Convergent Synthesis of the C12-C36 Fragment.
Fuwa, Haruhiko; Matsukida, Seiji; Miyoshi, Taro; Kawashima, Yuki; Saito, Tomoyuki; Sasaki, Makoto.
Afiliación
  • Fuwa H; Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
  • Matsukida S; Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
  • Miyoshi T; Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
  • Kawashima Y; Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
  • Saito T; Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
  • Sasaki M; Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
J Org Chem ; 81(6): 2213-27, 2016 Mar 18.
Article en En | MEDLINE | ID: mdl-26751853
Goniodomin A is a marine polyether macrolide natural product isolated from the dinoflagellate Alexandrium hiranoi. In this paper, we report stereocontrolled, convergent synthesis of a fully functionalized C12-C36 fragment of goniodomin A. The synthesis of the C12-C25 vinylstannane involved a Wittig reaction and a reductive cycloetherification for the construction of the dihydropyran ring. The C26-C36 thioester was synthesized via a Nozaki-Hiyama-Kishi reaction of an aldehyde and an iodoalkyne, the former of which was easily prepared from (R)-malic acid as a chiral source by taking advantage of substrate-controlled diastereoselective reactions. Finally, a palladium-catalyzed coupling of the C12-C25 vinylstannane and the C26-C36 thioester completed the synthesis of the target compound.
Asunto(s)
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Macrólidos / Éteres Idioma: En Revista: J Org Chem Año: 2016 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Macrólidos / Éteres Idioma: En Revista: J Org Chem Año: 2016 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos