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Chartspiroton, a Tetracyclic Spiro-naphthoquinone Derivative from a Medicinal Plant Endophytic Streptomyces.

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A novel 6/6/5/6 tetracyclic polyketide named chartspiroton (1) was isolated from a medicinal plant endophytic Streptomyces in Dendrobium officinale. The complete structure assignment with absolute stereochemistry was elucidated through spectroscopic… Click to show full abstract

A novel 6/6/5/6 tetracyclic polyketide named chartspiroton (1) was isolated from a medicinal plant endophytic Streptomyces in Dendrobium officinale. The complete structure assignment with absolute stereochemistry was elucidated through spectroscopic data, computational calculations, and single-crystal X-ray diffraction. Chartspiroton features an unprecedented naphthoquinone derivative spiro-fused with a benzofuran lactone moiety. A plausible polyketide biosynthetic pathway for 1 suggested intriguing oxidative rearrangement steps to form the five-membered lactone ring.

Keywords: plant endophytic; endophytic streptomyces; spiro; naphthoquinone derivative; medicinal plant

Journal Title: Organic letters
Year Published: 2020

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