Abstract
A general synthesis of anthraquinones which depends on the displacement of the methoxy group from an o-methoxyaryldihydro-oxazole by a methoxy substituted benzylmagnesium chloride, generated by using a magnesium-anthracene complex, has been developed. The masked benzyl-benzoic acids which result from these reactions are deprotected and then ring-closed to anthrones which on oxidation yield anthraquinones. In this way, the following naturally occurring anthraquinones (or derivatives thereof have been synthesized): chrysophanol (9), islandicin (19), digitopurpone (21), tri-O-methylemodin (26), and di-O-methylsoranjidiol (29).
| Original language | English |
|---|---|
| Pages (from-to) | 133-138 |
| Number of pages | 6 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Jan 1990 |
| Externally published | Yes |
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Nicoletti, T. M., Raston, C. L., & Sargent, M. V. (1990). A new synthesis of anthraquinones using dihydro-oxazoles and Grignard reagents derived from Mg(Anthracene)(THF)31. Journal of the Chemical Society, Perkin Transactions 1, (1), 133-138. https://doi.org/10.1039/P19900000133