40 Acorane-Alaskane型セスキテルペンの合成研究

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• Stereochemistry of the spirodienone esters 7a and 7b obtained by the intramolecular cyclization of phenolic bromo ester 9 was established by ^<13>C-NMR spectral analysis and chemical transformation to trans- and cis-1,4-dimethyltetralins 13a and 13b. It was proved that the cis-isomer 7b was the stable form. Compounds 7a and 7b were treated with a large excess of methyl lithium followed by a Lewis acid [SiO_2 for 7a and Mg(ClO_4)_2 for 7b] treatment to give tricyclic dienes 8a and 8b in 37 and 90% yields, respectively. The metal-ammonia reduction [Li (20 equiv.)/NH_3/THF/ t-BuOH/-40°] of 8a gave (±)-β-acorenol 2 in 81% yield. On the other hand, 8b afforded a mixture of 4-epi-β-acorenol 18 (10%), a disubstituted olefin 19 (66%) and a perhydro compound 20 (20%) under the same conditions. The yield of 18 was raised to 25% by altering the reaction conditions [Na (8 equiv.)/NH_3/THF/t-BuOH/-20°]. Dehydration (Al_2O_3/Py/200°) of 18 gave 4-epi-β-acoradiene 17 (78%), which was reduced with Li/EtNH_2 to give 16 (75%). (±)-Acorenone 5 was obtained by the allylic oxidation of 16 with SeO_2 in 70% yield.

• 天然有機化合物討論会の論文
• 1983-09-15

著者

• 岩田 宙造

  阪大・薬

• 前崎 直容

  阪大・薬

• 田中 徹明

  阪大・薬

• 中村 静夫

  Faculty Of Pharmaceutical Sciences Osaka University

• 上辻 秀和

  Faculty Of Pharmaceutical Sciences Osaka University

• 前崎 直容

  阪大院薬

• Tanaka T

  Osaka Univ. Osaka Jpn

• 符阪 隆文

  Faculty of Pharmaceutical Sciences, Osaka University

• 岸本 みちえ

  Faculty of Pharmaceutical Sciences, Osaka University

• 中村 静夫

  阪大・薬

• 篠尾 恭隆

  阪大・薬

• 符阪 隆文

  阪大・薬

• 岸本 みちえ

  阪大・薬

• 上辻 秀和

  阪大・薬

• 篠尾 恭隆

  Faculty Of Pharmaceutical Sciences Osaka University

• 岸本 みちえ

  Faculty Of Pharmaceutical Sciences Osaka University

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