Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

TETRAHEDRON

卷:67

Article

Shioe, Kazuma¹  Sahara, Yusuke²  Horino, Yoshikazu¹  Harayama, Takashi²  Takeuchi, Yasuo²  Abe, Hitoshi¹ 

[1] Toyama Univ, Grad Sch Sci & Engn, Toyama 9308555, Japan

[2] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, Okayama 7008530, Japan

关键词: Natural product;    Ellagitannin;    Axial chirality;    Palladium;    Regioisomer;   

DOI  :  10.1016/j.tet.2011.01.004

来源: Elsevier

【 摘 要 】

Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.

【 授权许可】

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