Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin

Hajime Yokoyama; Kumiko Otaya; Hisatake Kobayashi; Masahiro Miyazawa; Seiji Yamaguchi; Yoshiro Hirai

doi:10.1021/ol0060432

Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin

Hajime Yokoyama, Kumiko Otaya, Hisatake Kobayashi, Masahiro Miyazawa, Seiji Yamaguchi, Yoshiro Hirai^*

^*Corresponding author for this work

Department of Chemistry

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

89 Scopus citations

Abstract

(equation presented) The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.

Original language	English
Pages (from-to)	2427-2429
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	16
DOIs	https://doi.org/10.1021/ol0060432
State	Published - 2000/08/10

ASJC Scopus subject areas

Organic Chemistry
Drug Discovery
Biochemistry

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title = "Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin",

abstract = "(equation presented) The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.",

author = "Hajime Yokoyama and Kumiko Otaya and Hisatake Kobayashi and Masahiro Miyazawa and Seiji Yamaguchi and Yoshiro Hirai",

year = "2000",

month = aug,

day = "10",

doi = "10.1021/ol0060432",

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journal = "Organic Letters",

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T1 - Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin

AU - Yokoyama, Hajime

AU - Otaya, Kumiko

AU - Kobayashi, Hisatake

AU - Miyazawa, Masahiro

AU - Yamaguchi, Seiji

AU - Hirai, Yoshiro

PY - 2000/8/10

Y1 - 2000/8/10

N2 - (equation presented) The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.

AB - (equation presented) The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.

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U2 - 10.1021/ol0060432

DO - 10.1021/ol0060432

M3 - 学術論文

C2 - 10956513

AN - SCOPUS:0034632383

SN - 1523-7060

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SP - 2427

EP - 2429

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin

Abstract

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