A Synthesis of Polycyclic Aromatic Compounds by the Ca(OAc)2-Induced Aromatization of Polyoxoalkanedioates Generated from Diesters and Acetoacetate Dianion

Masahiko Yamaguchi; Koichi Hasebe; Hirofumi Higashi; Minoru Uchida; Akemi Irie; Toru Minami

doi:10.1021/jo00292a041

A Synthesis of Polycyclic Aromatic Compounds by the Ca(OAc)₂-Induced Aromatization of Polyoxoalkanedioates Generated from Diesters and Acetoacetate Dianion

Masahiko Yamaguchi, Koichi Hasebe, Hirofumi Higashi, Minoru Uchida, Akemi Irie, Toru Minami

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

40 Citations (Scopus)

Abstract

The dual-Claisen condensation of diesters with acetoacetate dianion generated tetraoxoalkanedioates, whose aromatization by Ca(OAc)₂-promoted intramolecular condensation constructed two carbocyclic rings containing phenol part. The reactions converted glutarates to bicyclic phenols and homophthalates to 1,9-dihydroxy-anthracenes. The latters were air-oxidized to anthraquinones in the presence of K₂CO₃. The regiochemistry of the arene synthesis was studied. As the products of this synthesis also were glutarates, further extension of the aromatic ring system was carried out. Pentacenequinones were synthesized from anthracenes, while an-thraquinones gave naphthacenequinones. The reactions are related to the biosynthesis of polycyclic aromatic compounds, and arenes obtained are useful intermediates in the natural products synthesis. A formal synthesis of aklavinone was achieved.

Original language	English
Pages (from-to)	1611-1623
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	55
Issue number	5
DOIs	https://doi.org/10.1021/jo00292a041
Publication status	Published - 1990 Jan 1
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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A Synthesis of Polycyclic Aromatic Compounds by the Ca(OAc)₂-Induced Aromatization of Polyoxoalkanedioates Generated from Diesters and Acetoacetate Dianion. / Yamaguchi, Masahiko; Hasebe, Koichi; Higashi, Hirofumi; Uchida, Minoru; Irie, Akemi; Minami, Toru.

In: Journal of Organic Chemistry, Vol. 55, No. 5, 01.01.1990, p. 1611-1623.

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

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abstract = "The dual-Claisen condensation of diesters with acetoacetate dianion generated tetraoxoalkanedioates, whose aromatization by Ca(OAc)2-promoted intramolecular condensation constructed two carbocyclic rings containing phenol part. The reactions converted glutarates to bicyclic phenols and homophthalates to 1,9-dihydroxy-anthracenes. The latters were air-oxidized to anthraquinones in the presence of K2CO3. The regiochemistry of the arene synthesis was studied. As the products of this synthesis also were glutarates, further extension of the aromatic ring system was carried out. Pentacenequinones were synthesized from anthracenes, while an-thraquinones gave naphthacenequinones. The reactions are related to the biosynthesis of polycyclic aromatic compounds, and arenes obtained are useful intermediates in the natural products synthesis. A formal synthesis of aklavinone was achieved.",

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AU - Yamaguchi, Masahiko

AU - Hasebe, Koichi

AU - Higashi, Hirofumi

AU - Uchida, Minoru

AU - Irie, Akemi

AU - Minami, Toru

PY - 1990/1/1

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N2 - The dual-Claisen condensation of diesters with acetoacetate dianion generated tetraoxoalkanedioates, whose aromatization by Ca(OAc)2-promoted intramolecular condensation constructed two carbocyclic rings containing phenol part. The reactions converted glutarates to bicyclic phenols and homophthalates to 1,9-dihydroxy-anthracenes. The latters were air-oxidized to anthraquinones in the presence of K2CO3. The regiochemistry of the arene synthesis was studied. As the products of this synthesis also were glutarates, further extension of the aromatic ring system was carried out. Pentacenequinones were synthesized from anthracenes, while an-thraquinones gave naphthacenequinones. The reactions are related to the biosynthesis of polycyclic aromatic compounds, and arenes obtained are useful intermediates in the natural products synthesis. A formal synthesis of aklavinone was achieved.

AB - The dual-Claisen condensation of diesters with acetoacetate dianion generated tetraoxoalkanedioates, whose aromatization by Ca(OAc)2-promoted intramolecular condensation constructed two carbocyclic rings containing phenol part. The reactions converted glutarates to bicyclic phenols and homophthalates to 1,9-dihydroxy-anthracenes. The latters were air-oxidized to anthraquinones in the presence of K2CO3. The regiochemistry of the arene synthesis was studied. As the products of this synthesis also were glutarates, further extension of the aromatic ring system was carried out. Pentacenequinones were synthesized from anthracenes, while an-thraquinones gave naphthacenequinones. The reactions are related to the biosynthesis of polycyclic aromatic compounds, and arenes obtained are useful intermediates in the natural products synthesis. A formal synthesis of aklavinone was achieved.

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