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

Kazuma Shioe, Yusuke Sahara, Yoshikazu Horino, Takashi Harayama, Yasuo Takeuchi, Hitoshi Abe

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1960-1970
Number of pages11
JournalTetrahedron
Volume67
Issue number10
DOIs
Publication statusPublished - Mar 11 2011

Keywords

  • Axial chirality
  • Ellagitannin
  • Natural product
  • Palladium
  • Regioisomer

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B'. Together they form a unique fingerprint.

  • Cite this

    Shioe, K., Sahara, Y., Horino, Y., Harayama, T., Takeuchi, Y., & Abe, H. (2011). Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B. Tetrahedron, 67(10), 1960-1970. https://doi.org/10.1016/j.tet.2011.01.004