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Review | Regular issue | Vol 100, No. 2, 2020, pp.177-193
Published online, 23rd December, 2019
DOI: 10.3987/REV-19-915
Chemistry of Anti-HIV Active Trimeric Pyranonaphthoquinone Conocurvone: Synthetic Studies towards Monomeric Teretifolione B and Related Compounds

Takuya Kumamoto* and Kazuaki Katakawa

*Department of Synthetic Organic Chemistry, School of Pharmaceutical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan

Abstract

Pyranonaphthoquinone natural products are widely distributed in plants and microorganisms and have diverse biological activities. Angular benzochromenes are a small class of natural products isolated from Conospermum and Pentas plants. Of these, conocurvone was isolated from Conospermum as a trimeric pyranonaphthoquinone that has potent anti-HIV activity. We have focused on the total synthesis of compounds that exhibit biological activity or whose activity is enhanced upon oligomerization. This review describes the discovery and biological activities of the trimeric pyranonaphthoquinone conocurvone and related compounds, as well as our and other researchers’ synthetic studies toward monomeric pyranonaphthoquinones.