Synthesis of Allene-Containing Apocarotenoids by Cross-Coupling Strategy

Kazuhiko Sakaguchi; Yuto Nishioka; Naoto Kinashi; Nao Yukihira; Tetsuro Shinada; Takahiro Nishimura; Hideki Hashimoto; Shigeo Katsumura

doi:10.1055/s-0040-1707906

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(20): 3007-3017
DOI: 10.1055/s-0040-1707906

paper

Synthesis of Allene-Containing Apocarotenoids by Cross-Coupling Strategy

Kazuhiko Sakaguchi ∗

^aDivision of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan eMail: sakaguch@sci.osaka-cu.ac.jp

,

Yuto Nishioka

^aDivision of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan eMail: sakaguch@sci.osaka-cu.ac.jp

,

Naoto Kinashi

^aDivision of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan eMail: sakaguch@sci.osaka-cu.ac.jp

,

Nao Yukihira

^bSchool of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo, 669-1337, Japan

,

Tetsuro Shinada

^aDivision of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan eMail: sakaguch@sci.osaka-cu.ac.jp

,

Takahiro Nishimura

^aDivision of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan eMail: sakaguch@sci.osaka-cu.ac.jp

,

Hideki Hashimoto

^bSchool of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo, 669-1337, Japan

,

Shigeo Katsumura

^aDivision of Molecular Materials Science, Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan eMail: sakaguch@sci.osaka-cu.ac.jp

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Abstract

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Abstract

The stereocontrolled total synthesis of the allene and carbonyl conjugated apocarotenoids, paracentrone and 19-hexanoyloxyparacentrone 3-acetate, was achieved by sequential cross-coupling reactions using boronic acid ester and iodine- or tin-substituted C5 dienes, which were the building blocks for the elongation of the conjugated polyene systems at both terminals.

Key words

apocarotenoid - paracentrone - fucoxanthin - cross-coupling - C5 diene - allene

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Referenzen

References and Notes
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