15 有機イオウ化合物を用いるα-cis-Bergamotene,Jasmone類の新しい合成法

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The syntheses of α-cis-bergamotene and jasmone derivatives were studied by utilizing new reactions developed by the use of organo sulfur compounds. I. Lithium salt of dimethylally 2-pyridylsulfide was treated with 9-iodo-α-pinene(6) to yield α-alkylated product(7), which was reduced with CuCl_2-LiAlH_4 to afford α-cis-bergamotene(5). IIa). 2-Methylcyclopentanone was easily converted to 5,5-bis(phenylthio) derivative(11) by the reaction with sulfenamide. Then 11 was alkylated with triallylborane and hydrolysis and dehydration of 12 with AgClO_4 afforded allyl-rethrone(9). b). Di[bis(phenylthio)alkylmethyl] copper lithium was react with conjugated enones and 1,4 addition products(14) were exclusively obtained. The products(14) was converted quantitatively into 1,4-diketone(15) by hydrolysis with CuCl_2-CuO. By this method dihydrojasmone(16) was obtained from heptanal diphenylthioacetal in only 3 steps.
天然有機化合物討論会の論文
1972-10-01