Synthesis and absolute structure of (-)-umtatin

Seiji Yamaguchi; Masahide Kobayashi; Shin Ichiro Harada; Masahiro Miyazawa; Yoshiro Hirai

doi:10.1246/bcsj.81.863

Synthesis and absolute structure of (-)-umtatin

Seiji Yamaguchi^*, Masahide Kobayashi, Shin Ichiro Harada, Masahiro Miyazawa, Yoshiro Hirai

^*Corresponding author for this work

Department of Chemistry

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

5 Scopus citations

Abstract

A new preparation of 2-(hydroxymethyl)chromones was developed via the new regio-selective six-membered cyclization of 1-[o-(tert-butyldimethylsiloxy) phenyl]but-2-yn-1-ones by a three-step treatment with 1) diethylamine (activation of the γ-position), 2) KF-18-crown-6 (deprotection), and 3) silica-gel (cyclization). A naturally occurring chiral hydroxymethylfurochromone, (-)-umtatin, was synthesized starting from chiral (R)-(-)-2-isopropenyl-4,6-dimethoxy-2,3-dihydrobenzofuran, and the absolute structure was determined to R.

Original language	English
Pages (from-to)	863-868
Number of pages	6
Journal	Bulletin of the Chemical Society of Japan
Volume	81
Issue number	7
DOIs	https://doi.org/10.1246/bcsj.81.863
State	Published - 2008/07/15

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General Chemistry

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title = "Synthesis and absolute structure of (-)-umtatin",

abstract = "A new preparation of 2-(hydroxymethyl)chromones was developed via the new regio-selective six-membered cyclization of 1-[o-(tert-butyldimethylsiloxy) phenyl]but-2-yn-1-ones by a three-step treatment with 1) diethylamine (activation of the γ-position), 2) KF-18-crown-6 (deprotection), and 3) silica-gel (cyclization). A naturally occurring chiral hydroxymethylfurochromone, (-)-umtatin, was synthesized starting from chiral (R)-(-)-2-isopropenyl-4,6-dimethoxy-2,3-dihydrobenzofuran, and the absolute structure was determined to R.",

author = "Seiji Yamaguchi and Masahide Kobayashi and Harada, {Shin Ichiro} and Masahiro Miyazawa and Yoshiro Hirai",

year = "2008",

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doi = "10.1246/bcsj.81.863",

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T1 - Synthesis and absolute structure of (-)-umtatin

AU - Yamaguchi, Seiji

AU - Kobayashi, Masahide

AU - Harada, Shin Ichiro

AU - Miyazawa, Masahiro

AU - Hirai, Yoshiro

PY - 2008/7/15

Y1 - 2008/7/15

N2 - A new preparation of 2-(hydroxymethyl)chromones was developed via the new regio-selective six-membered cyclization of 1-[o-(tert-butyldimethylsiloxy) phenyl]but-2-yn-1-ones by a three-step treatment with 1) diethylamine (activation of the γ-position), 2) KF-18-crown-6 (deprotection), and 3) silica-gel (cyclization). A naturally occurring chiral hydroxymethylfurochromone, (-)-umtatin, was synthesized starting from chiral (R)-(-)-2-isopropenyl-4,6-dimethoxy-2,3-dihydrobenzofuran, and the absolute structure was determined to R.

AB - A new preparation of 2-(hydroxymethyl)chromones was developed via the new regio-selective six-membered cyclization of 1-[o-(tert-butyldimethylsiloxy) phenyl]but-2-yn-1-ones by a three-step treatment with 1) diethylamine (activation of the γ-position), 2) KF-18-crown-6 (deprotection), and 3) silica-gel (cyclization). A naturally occurring chiral hydroxymethylfurochromone, (-)-umtatin, was synthesized starting from chiral (R)-(-)-2-isopropenyl-4,6-dimethoxy-2,3-dihydrobenzofuran, and the absolute structure was determined to R.

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U2 - 10.1246/bcsj.81.863

DO - 10.1246/bcsj.81.863

M3 - 学術論文

AN - SCOPUS:58149267906

SN - 0009-2673

VL - 81

SP - 863

EP - 868

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

IS - 7

ER -

Synthesis and absolute structure of (-)-umtatin

Abstract

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