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Short Paper | Regular issue | Vol 98, No. 2, 2019, pp.281-294
Published online, 13th February, 2019
DOI: 10.3987/COM-18-S(F)91
Synthetic Study of an Intermediates towards Paracentrone

Taiki Kaneyama, Kazumi Fujimaru, Mami Takemura, Kizuku Hasegawa, Masahiro Hamada, Takao Kishimoto, Daisuke Urabe, and Noriyuki Nakajima*

*Faculty of Engineering, Toyama Prefectural University, 5180 Kurokawa, Kosugi, Toyama 939-0398, Japan

Abstract

Paracentrone (1), the second naturally occurring C31-methyl ketone apocarotenoid from fucoxanthin (2), was first isolated from the sea urchin Paracentrotus lividus. In this study, we focused on this carotenoid metabolite and report on a synthetic approach towards (3E)-(5R)-[(2R,4S)-2-hydroxyl-4-(tert-butyldimethylsilyl)oxy-2,6,6-trimethylcyclohexylidene]-1-iodo-4-methyl-1,3,5-hexatriene (5), a synthetic intermediate towards 1. This was obtained from epoxy acetylene (11) via (2E)-(4R)-[(2R,4S)-2-hydroxyl-4-(tert-butyldimethylsilyl)oxy-2,6,6-trimethylcyclohexylidene]-3-methylpenta-2,4-diene-1-ol (7).