Abstract
As forecast in the preceding communication, we have now succeeded in synthesizing natural racemic cinerolone and thence of cinerin-I. The sodium salt, obtained by hydrolysis with 3 per cent sodium hydroxide at 20° of methyl cis-hept-5-en-2-one-1-carboxylate, an intermediate in the previous synthesis, was condensed with pyruvaldehyde in aqueous solution at 35° and pH 8·5 to give cis-dec-8-en-3-ol-2: 5-dione. This hydroxydiketone was cyclized by 2 per cent sodium hydroxide at 20° to (±)-cis-cinerolone (II). The semicarbazones of this hydroxyketone and of its acetate (see the table) were shown by mixestrictly cinerond melting point determinations to be identical with naturally derived racemic cinerolone and cinerolone (strictly cineronyl) acetate semicarbazones respectively. Specimens of the corresponding (±)-trans-cinerolone derivatives (prepared in collaboration with A. J. B. Edgar) markedly depressed the melting points of both the natural and synthetic (±)-cis-cinerolone derivatives.
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CROMBŒ, L., HARPER, S. Synthesis of Cinerone, Cinerolone and of Cinerin-I. Nature 164, 535 (1949). https://doi.org/10.1038/164535a0
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DOI: https://doi.org/10.1038/164535a0
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