Synthesis of the Tetracyclic Spiro-naphthoquinone Chartspiroton.
| Autor: | Röder L; Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria., Wurst K; Department of General Inorganic and Theoretical Chemistry, University of Innsbruck, 6020 Innsbruck, Austria., Magauer T; Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria. |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2024 Apr 19; Vol. 26 (15), pp. 3065-3068. Date of Electronic Publication: 2024 Apr 01. |
| DOI: | 10.1021/acs.orglett.4c00695 |
| Abstrakt: | Chartspiroton is a recently discovered naphthoquinone natural product that features a spiro-fused benzofuran lactone. We report its first synthesis via an 11-step linear sequence. The sterically hindered tetra- ortho -substituted biaryl subunit was installed by base-induced ring expansion of a readily available 1,3-indandione. This step also liberated the fully substituted naphthalene core unit at the same time. The unique spiro-fused benzofuran lactone of the natural product was constructed via late-stage oxidation of an advanced naphthoquinone. |
| Databáze: | MEDLINE |
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