Synthesis of larreantin, a cytotoxic naphthoquinonoid sesquilignan from Larrea tridentata
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 23 (11) , 2783-2787
- https://doi.org/10.1039/p19910002783
Abstract
Larreantin [8-(4-hydroxy-3-methoxyphenyl)-6-(4-hydroxy-3-methoxybenzyl)-2-methoxy-7-methyl-naphthalene-1,4-dione]1, a biogenetically unique cytotoxic naphthoquinonoid sesquilignan has been synthesized by a convergent route. The key intermediate was 4,5-dihydro-2-(5,7-diisopropoxy-1methoxy-2-naphthyl)-4,4-dimethyloxazole 14 which was elaborated by treatment with 4-isopropoxy-3-methoxyphenylmagnesium bromide 26 and the product of this reaction was lithiated and allowed to react with 4-isoproproxy-3-methoxybenzaldehyde 28. Subsequent steps then gave larreantin 1.Keywords
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