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

Fingerprint

Hydrolyzable Tannins
Lactones
Bioactivity
Sugars
Esters
ellagitannin
isorugosin B

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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

Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B. / Shioe, Kazuma; Sahara, Yusuke; Horino, Yoshikazu; Harayama, Takashi; Takeuchi, Yasuo; Abe, Hitoshi.

In: Tetrahedron, Vol. 67, No. 10, 11.03.2011, p. 1960-1970.

Research output: Contribution to journalArticle

Shioe, K, Sahara, Y, Horino, Y, Harayama, T, Takeuchi, Y & Abe, H 2011, 'Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B', Tetrahedron, vol. 67, no. 10, pp. 1960-1970. https://doi.org/10.1016/j.tet.2011.01.004
Shioe, Kazuma ; Sahara, Yusuke ; Horino, Yoshikazu ; Harayama, Takashi ; Takeuchi, Yasuo ; Abe, Hitoshi. / Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B. In: Tetrahedron. 2011 ; Vol. 67, No. 10. pp. 1960-1970.
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