Aryl-β-C-glucosidation using glucal boronate: Application to the synthesis of tri-O-methylnorbergenin

Shigeki Sakamaki, Eiji Kawanishi, Sumihiro Nomura, Tsutomu Ishikawa

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Novel aryl-β-C-glucosidation method using glucal boronate was developed. This protocol can offer several advantages including use of non-toxic, easily handling glucal boronate as a crystalline solid and storable at room temperature for several months. Tri-O-methylnorbergenin (8,10-di-O-methylbergenin), an anti-HIV active bergenin derivative, was concisely synthesized by application of the aryl-β-C-glucosidation method.

Original languageEnglish
Pages (from-to)5744-5753
Number of pages10
JournalTetrahedron
Volume68
Issue number29
DOIs
Publication statusPublished - Jul 22 2012
Externally publishedYes

Fingerprint

Calcium Gluconate
HIV
Crystalline materials
Derivatives
Temperature
8,10-di-O-methylbergenin
bergenin
caN protocol

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Aryl-β-C-glucosidation using glucal boronate : Application to the synthesis of tri-O-methylnorbergenin. / Sakamaki, Shigeki; Kawanishi, Eiji; Nomura, Sumihiro; Ishikawa, Tsutomu.

In: Tetrahedron, Vol. 68, No. 29, 22.07.2012, p. 5744-5753.

Research output: Contribution to journalArticle

Sakamaki, Shigeki ; Kawanishi, Eiji ; Nomura, Sumihiro ; Ishikawa, Tsutomu. / Aryl-β-C-glucosidation using glucal boronate : Application to the synthesis of tri-O-methylnorbergenin. In: Tetrahedron. 2012 ; Vol. 68, No. 29. pp. 5744-5753.
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