A new approach toward the total synthesis of (+)-batzellaside B

Beilstein Journal of Organic Chemistry

Hidemi Yoda¹  Jolanta Wierzejska¹  Tetsuya Sengoku¹  Masaki Takahashi¹  Yuto Makino¹  Shin-ichi Motogoe¹ 

[1] Department of Materials Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Naka-ku, Hamamatsu, Shizuoka 432-8561, Japan;

关键词: asymmetric dihydroxylation;    (+)-batzellaside B;    iminosugar;    L-pyroglutamic acid;    total synthesis;   

DOI  :  10.3762/bjoc.8.210

来源: DOAJ

【 摘 要 】

A new synthetic approach to (+)-batzellaside B from naturally abundant L-pyroglutamic acid is presented in this article. The key synthetic step involves Sharpless asymmetric dihydroxylation of an olefinic substrate functionalized with an acetoxy group to introduce two chiral centres diastereoselectively into the structure. Heterocyclic hemiaminal 4, which could be converted from the resulting product, was found to provide stereospecific access to enantiomerically enriched allylated intermediate, offering better prospects for the total synthesis of this natural product.

【 授权许可】

Unknown