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Short Paper | Special issue | Vol 103, No. 2, 2021, pp.1064-1077
Published online, 15th February, 2021
DOI: 10.3987/COM-20-S(K)60
Total Synthesis of (±)-4-Deoxyblennolide C via Spirochromanone

Takuya Kumamoto,* Sho Hasegawa, Kanna Adachi, and Kazuaki Katakawa

*Department of Synthetic Organic Chemistry, Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi Minami-ku, Hiroshima, 734-8553, Japan

Abstract

We report the total synthesis of (±)-4-deoxyblennolide C, a deoxy analogue of xanthone antibiotics blennolide C isolated from the fermentation broth of Blennoria sp. The synthesis involves construction of a quaternary carbon during the formation of spirochromanone through the aldol reaction of o-hydroxyacetophenones and cyclohexenone, oxidative cleavage of the alkene moiety, and the construction of a xanthone framework by Dieckmann condensation.