Synthesis 2020; 52(20): 3007-3017
DOI: 10.1055/s-0040-1707906
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Allene-Containing Apocarotenoids by Cross-Coupling Strategy

a   Division 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
a   Division 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
a   Division 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
b   School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo, 669-1337, Japan
,
a   Division 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
,
a   Division 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
b   School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo, 669-1337, Japan
,
Shigeo Katsumura
a   Division 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
› Institutsangaben
This study was supported by KAKENHI Grant Number 24106741, 17H06433 and 17H0637 from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, and KAKENHI Grant Numbers 25410183, 26410183, 16H04181 and 17K05935 from the Japan Society of the Promotion of Science (JSPS).
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Publikationsverlauf

Received: 26. Mai 2020

Accepted after revision: 25. Juni 2020

Publikationsdatum:
21. Juli 2020 (online)


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.

Supporting Information