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Expedient Synthesis of Alphitolic Acid and Its Naturally Occurring 2- O-Ester Derivatives.
Park, Somin; Cho, Jihee; Jeon, Hongjun; Sung, Sang Hyun; Lee, Seunghee; Kim, Sanghee.
Afiliación
  • Park S; College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
  • Cho J; College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
  • Jeon H; College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
  • Sung SH; College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
  • Lee S; College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
  • Kim S; College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
J Nat Prod ; 82(4): 895-902, 2019 04 26.
Article en En | MEDLINE | ID: mdl-30768265
The expedient synthesis of alphitolic acid (1) as well as its natural C-3-epimer and 2- O-ester derivatives was accomplished in a few steps from the readily commercially available betulin (9). A Rubottom oxidation delivered an α-hydroxy group in a stereo- and chemoselective manner. The diastereoselective reduction of the α-hydroxy ketone was key to accessing the 1,2-diol moiety of this class of natural products. Our concise and stereoselective synthetic protocol allowed the gram-scale synthesis of these natural products, which will facilitate future biological evaluations.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Triterpenos / Productos Biológicos Idioma: En Revista: J Nat Prod Año: 2019 Tipo del documento: Article Pais de publicación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Triterpenos / Productos Biológicos Idioma: En Revista: J Nat Prod Año: 2019 Tipo del documento: Article Pais de publicación: Estados Unidos