Synthesis of 2-Alkyl-2-(2-furanyl)-1,3-cyclopentanediones

Kazutada Ikeuchi; Yusuke Ozoe; Ranmaru Kato; Takahiro Suzuki; Keiji Tanino

doi:10.1055/a-2004-1333

Synthesis, Table of Contents

Synthesis 2023; 55(10): 1525-1532
DOI: 10.1055/a-2004-1333

paper

Synthesis of 2-Alkyl-2-(2-furanyl)-1,3-cyclopentanediones

Kazutada Ikeuchi ∗

^aDepartment of Chemistry, Faculty of Science, Hokkaido University, Kita 10, nishi 8, kita-ku, Sapporo 060-0810, Japan

,

Yusuke Ozoe

^bGraduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13, nishi 8, kita-ku, Sapporo 060-0810, Japan

,

Ranmaru Kato

^bGraduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13, nishi 8, kita-ku, Sapporo 060-0810, Japan

,

Takahiro Suzuki

^aDepartment of Chemistry, Faculty of Science, Hokkaido University, Kita 10, nishi 8, kita-ku, Sapporo 060-0810, Japan

,

Keiji Tanino ∗

^aDepartment of Chemistry, Faculty of Science, Hokkaido University, Kita 10, nishi 8, kita-ku, Sapporo 060-0810, Japan

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Abstract

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Abstract

2,2-Disubstituted 1,3-cyclopentanediones are versatile building blocks for synthesizing complex natural products with bicyclic structures including cyclopentane rings. The reported method for the synthesis of these compounds involves the semi-pinacol rearrangement of a Mukaiyama aldol adduct prepared from a ketone/ketal and 1,2-bis(trimethylsilyloxy)cyclobutene. However, the adoption of α-oxy-functionalized ketones/ketals is quite difficult, as demonstrated by our experiments. To overcome this limitation of the method, 2-acylfuran derivatives were used as the reactants to synthesize 2,2-disubstituted 1,3-cyclopentanediones. Furthermore, two reaction conditions, that is, the use of 1.4 equivalents of a boron trifluoride-diethyl ether complex or 0.4 and 0.2 equivalent of trimethylsilyl triflate and methoxytrimethylsilane, respectively, were established for the conversion of 2-acylfurans into the corresponding 1,3-cyclopentanediones in acceptable yields. The transformations of the furan rings in the obtained products were also investigated.

Key words

1,3-cyclopentanedione - 1,2-bis(trimethylsilyloxy)cyclobutene - 2-acylfuran - semi-pinacol rearrangement - trimethylsilyl triflate

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References

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