16 オーキシンbラクトンの合成
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The compound having the proposed structure for auxin b lactone (III) was synthesized as follows: 2,4-Di-s-butylphenol (IV) which was prepared through several steps from anisol was hydrogenated at high pressure and temperature in the presence of Raney nickel to 2,4-di-s-butylcyclohexanol (V). When the cyclohexanol was oxidized with potassium dichromate in dilute sulfuric acid, 2,4-di-s-butylcyclohexanone (VI) could be obtained in high yield, and the latter compound was further oxidized with ferric chloride to 3,5-di-s-butylcyclohexane-I,2-dione (VII). Reduction of this dione yielded 3,5-di-s-butylcyclohexane-I,2-diol (VIII), which was treated with lead tetraacetate in dry chloroform; and the obtained dialdehyde, without further purification, was immediately cyclized and dehydrated with piperidine acetate in benzene to 3,5-di-s-butyl-I-cyclopentene-aldehyde (IX) in 82% yield. The Reformatsky reaction of IX with ethyl γ-bromo-β-ethoxycrotonate afforded 4-ethoxy-6-(3,5-di-s-butyl-I-cyclopenten-I-yl)-5,6-dihydro-2-pyrone (X). After treating the enol ether with formic acid for 40 hours at room temperature, and purifying the crude acidic portion with column chromatography on silica gel, stereoisomeric mixture of 4-hydroxy-6-(3,5-di-s-butyl-I-cyclopenten-I-yl)-5,6-dihydro-2-pyrone (III), the compound having the proposed structure for auxin b lactone, was obtained as an oil. III was found to be active in Avena coleoptile section test, Avena root growth test, and pea stem section test; but inactive in Avena coleoptile curvature test and slit pea stem curvature test.
- 天然有機化合物討論会の論文
- 1966-09-15
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