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Abstract In this paper, skeletal rearrangements of 2-hydroxy-3-methyl-1,4-naphthoquinones to indanones are reported. The application of this reaction to the synthesis of an indanone isolated from root cultures of the West… Click to show full abstract
Abstract In this paper, skeletal rearrangements of 2-hydroxy-3-methyl-1,4-naphthoquinones to indanones are reported. The application of this reaction to the synthesis of an indanone isolated from root cultures of the West African liana Triphyophyllum peltatum is described. The spectroscopic data of this synthetic indanone are different from those reported for the natural product, indicating that the reported structure is incorrect. The structure was unambiguously revised through the synthesis of the compound with spectroscopic data identical to the natural product. A biosynthetic conversion of droserone, 3,5-dihydroxy-2-methyl-1,4-naphthoquinone, to this indanone is also proposed.
Journal Title: Tetrahedron Letters
Year Published: 2020
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