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Paper | Special issue | Vol 99, No. 1, 2019, pp.549-565
Published online, 14th December, 2018
DOI: 10.3987/COM-18-S(F)52
First Total Synthesis of Palmarumycin C6 Based on Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene to 3-Bromo-1-indenone

Hirokazu Tsukamoto, Yumi Nomura, and Takayuki Doi*

*Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan


Synthetic studies on palmarumycin C6 with a naphthyl acetal at the C-3 position in 4,7-dihydroxy-1-indanone as a lower homologue of spirobisnaphthalenes are described herein. We investigated three approaches: 1) Nazarov cyclization of benzoylketene acetal, 2) intramolecular Friedel-Crafts acylation of naphtho[1,8-de]-1,3-dioxin-2-aryl-2-acetic acid chloride, and 3) double oxa-Michael addition of 1,8-dihydroxynaphthalene to 3-bromo-1-indenone. The last approach successfully afforded the natural product after the removal of acetates that serve as protecting groups for phenolic hydroxyls under acidic conditions.