19533-92-7Relevant articles and documents
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
, p. 895 - 902 (2019/05/14)
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.
Efficient access to isomeric 2,3-dihydroxy lupanes: first synthesis of alphitolic acid
Hao, Jia,Zhang, Xueli,Zhang, Pu,Liu, Jun,Zhang, Luyong,Sun, Hongbin
experimental part, p. 7975 - 7984 (2009/12/06)
Alphitolic acid (3) is a naturally occurring lupane type of pentacyclic triterpene, which possesses various pharmacological properties. Efficient synthesis of 3 has been accomplished in 10 steps with an overall yield of 19% starting from the readily avail
