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Communication | Regular issue | Vol 106, No. 4, 2023, pp.641-648
Published online, 15th March, 2023
DOI: 10.3987/COM-23-14826
Synthesis of Maleimide-Fused Aceheptylenes from Guaiazulene

Taku Shoji,* Mayumi Uda, Tetsuo Okujima, Ryuta Sekiguchi, and Shunji Ito

*Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama 963-8642, Fukushima, Japan


Maleimide-fused aceheptylenes were prepared using guaizulene as a starting material. The condensation reaction of 3,4-diformylguaiazulene derivative, which was prepared in three steps from guaiazulene, with maleimides in the presence of tri-n-butylphosphine and 1,8-diazabicyclo[5.4.0]undec-7-ene afforded the maleimide-fused aceheptylenes. Structural feature of the aceheptylenes prepared was revealed by 1H NMR spectroscopy and nucleus-independent chemical shift calculations.