Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

Naoto Katoh; Takashi Nakahata; Shigefumi Kuwahara

doi:10.1016/j.tet.2008.07.023

Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

Naoto Katoh, Takashi Nakahata, Shigefumi Kuwahara

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

14 Citations (Scopus)

Abstract

Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product.

Original language	English
Pages (from-to)	9073-9077
Number of pages	5
Journal	Tetrahedron
Volume	64
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2008.07.023
Publication status	Published - 2008 Sep 15

Keywords

Alder-Rickert reaction
Phthalide
Take-all
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.07.023

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title = "Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus",

abstract = "Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product.",

keywords = "Alder-Rickert reaction, Phthalide, Take-all, Total synthesis",

author = "Naoto Katoh and Takashi Nakahata and Shigefumi Kuwahara",

note = "Funding Information: We thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 19380065).",

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T1 - Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

AU - Katoh, Naoto

AU - Nakahata, Takashi

AU - Kuwahara, Shigefumi

N1 - Funding Information: We thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 19380065).

PY - 2008/9/15

Y1 - 2008/9/15

N2 - Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product.

AB - Two antifungal phthalides produced by a wheat rhizosphere fungus have been synthesized using the Alder-Rickert reaction to construct their common isobenzofuranone core structure. The absolute configuration of one of the two phthalides has been determined to be S by synthesizing its (S)- and (R)-enantiomer and comparing their optical rotations with that of the natural product.

KW - Alder-Rickert reaction

KW - Phthalide

KW - Take-all

KW - Total synthesis

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JO - Tetrahedron

JF - Tetrahedron

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ER -

Synthesis of novel antifungal phthalides produced by a wheat rhizosphere fungus

Abstract

Keywords

ASJC Scopus subject areas

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