Synthesis of spiro C-arylglycoriboside via Pd(II)-catalyzed spirocyclization

Ken Ichiro Awasaguchi; Masahiro Miyazawa; Ikuyo Uoya; Koichi Inoue; Koji Nakamura; Hajime Yokoyama; Hiroko Kakuda; Yoshiro Hirai

doi:10.1055/s-0030-1258560

Synthesis of spiro C-arylglycoriboside via Pd(II)-catalyzed spirocyclization

Ken Ichiro Awasaguchi, Masahiro Miyazawa^*, Ikuyo Uoya, Koichi Inoue, Koji Nakamura, Hajime Yokoyama, Hiroko Kakuda, Yoshiro Hirai

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Spiro C-arylglycoriboside was synthesized in 21 steps via Pd(II)-catalyzed spirocyclization as a key reaction. Hemiketal was obtained in 47% overall yield from cis-2-butene-1,4-diol and spirocyclized with PdCl₂(PhCN) ₂ in dilute THF solution (0.01 M) to afford the 1,6-dioxaspiro[4.4] nonane skeleton in high yield. The spirocyclo adduct was transformed into spiro C-arylglycoriboside in five steps.

Original language	English
Pages (from-to)	2392-2396
Number of pages	5
Journal	Synlett
Issue number	16
DOIs	https://doi.org/10.1055/s-0030-1258560
State	Published - 2010

Keywords

cyclization
heterocycles
palladium
spiro compound
stereoselectivity

ASJC Scopus subject areas

Organic Chemistry
Drug Discovery

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title = "Synthesis of spiro C-arylglycoriboside via Pd(II)-catalyzed spirocyclization",

abstract = "Spiro C-arylglycoriboside was synthesized in 21 steps via Pd(II)-catalyzed spirocyclization as a key reaction. Hemiketal was obtained in 47% overall yield from cis-2-butene-1,4-diol and spirocyclized with PdCl2(PhCN) 2 in dilute THF solution (0.01 M) to afford the 1,6-dioxaspiro[4.4] nonane skeleton in high yield. The spirocyclo adduct was transformed into spiro C-arylglycoriboside in five steps.",

keywords = "cyclization, heterocycles, palladium, spiro compound, stereoselectivity",

author = "Awasaguchi, {Ken Ichiro} and Masahiro Miyazawa and Ikuyo Uoya and Koichi Inoue and Koji Nakamura and Hajime Yokoyama and Hiroko Kakuda and Yoshiro Hirai",

year = "2010",

doi = "10.1055/s-0030-1258560",

language = "英語",

pages = "2392--2396",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "16",

}

TY - JOUR

T1 - Synthesis of spiro C-arylglycoriboside via Pd(II)-catalyzed spirocyclization

AU - Awasaguchi, Ken Ichiro

AU - Miyazawa, Masahiro

AU - Uoya, Ikuyo

AU - Inoue, Koichi

AU - Nakamura, Koji

AU - Yokoyama, Hajime

AU - Kakuda, Hiroko

AU - Hirai, Yoshiro

PY - 2010

Y1 - 2010

N2 - Spiro C-arylglycoriboside was synthesized in 21 steps via Pd(II)-catalyzed spirocyclization as a key reaction. Hemiketal was obtained in 47% overall yield from cis-2-butene-1,4-diol and spirocyclized with PdCl2(PhCN) 2 in dilute THF solution (0.01 M) to afford the 1,6-dioxaspiro[4.4] nonane skeleton in high yield. The spirocyclo adduct was transformed into spiro C-arylglycoriboside in five steps.

AB - Spiro C-arylglycoriboside was synthesized in 21 steps via Pd(II)-catalyzed spirocyclization as a key reaction. Hemiketal was obtained in 47% overall yield from cis-2-butene-1,4-diol and spirocyclized with PdCl2(PhCN) 2 in dilute THF solution (0.01 M) to afford the 1,6-dioxaspiro[4.4] nonane skeleton in high yield. The spirocyclo adduct was transformed into spiro C-arylglycoriboside in five steps.

KW - cyclization

KW - heterocycles

KW - palladium

KW - spiro compound

KW - stereoselectivity

UR - http://www.scopus.com/inward/record.url?scp=77957113991&partnerID=8YFLogxK

U2 - 10.1055/s-0030-1258560

DO - 10.1055/s-0030-1258560

M3 - 学術論文

AN - SCOPUS:77957113991

SN - 0936-5214

SP - 2392

EP - 2396

JO - Synlett

JF - Synlett

IS - 16

ER -

Synthesis of spiro C-arylglycoriboside via Pd(II)-catalyzed spirocyclization

Abstract

Keywords

ASJC Scopus subject areas

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