Stereoselective Synthesis of Spirolactone Analogues of Pyrrolomorpholine Alkaloids.

Uchiyama, Ami; Ohta, Hikari; Ogawa, Yuya; Sasaki, Ikuo; Sugimura, Hideyuki

Uchiyama, Ami; Ohta, Hikari; Ogawa, Yuya; Sasaki, Ikuo; Sugimura, Hideyuki.

Afiliación

Uchiyama A; Department of Chemistry and Bioscience, Faculty of Science and Technology, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara 252-5258, Japan.
Ohta H; Department of Chemistry and Bioscience, Faculty of Science and Technology, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara 252-5258, Japan.
Ogawa Y; Department of Chemistry and Bioscience, Faculty of Science and Technology, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara 252-5258, Japan.
Sasaki I; Department of Chemistry and Bioscience, Faculty of Science and Technology, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara 252-5258, Japan.
Sugimura H; Department of Chemistry and Bioscience, Faculty of Science and Technology, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara 252-5258, Japan.

J Org Chem ; 89(17): 12864-12870, 2024 Sep 06.

Article en En | MEDLINE | ID: mdl-39163643

ABSTRACT

ABSTRACT

The synthesis of a spirolactone analogue of xylapyrraside B1, a potent antioxidant agent, is described. The key step is the stereoselective formation of the spirolactone skeleton via the formal [3+2] annulation of the isopropylidene-protected glyceraldehyde and Î´-methylene lactone, mediated by trifluoroborane etherate. This study addresses the stereoselective synthesis of pyrrolomorpholine spiroketal alkaloids, enabling the production of these bioactive compounds and their analogues.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos

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