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

Shigeki Sakamaki; Eiji Kawanishi; Sumihiro Nomura; Tsutomu Ishikawa

doi:10.1016/j.tet.2012.05.035

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 journal › Article › peer-review

32 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 language	English
Pages (from-to)	5744-5753
Number of pages	10
Journal	Tetrahedron
Volume	68
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2012.05.035
Publication status	Published - Jul 22 2012
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.05.035

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AU - Sakamaki, Shigeki

AU - Kawanishi, Eiji

AU - Nomura, Sumihiro

AU - Ishikawa, Tsutomu

PY - 2012/7/22

Y1 - 2012/7/22

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AB - 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.

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JF - Tetrahedron

IS - 29

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

UN SDGs

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