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.
Original language | English |
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Article number | 151494 |
Journal | Tetrahedron Letters |
Volume | 61 |
Issue number | 7 |
DOIs | |
Publication status | Published - 2020 Feb 13 |
Externally published | Yes |
Keywords
- 1,4-Naphthoquinone
- Indanone
- Skeletal rearrangement
- Structural revision
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry