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姜黄烯类倍半萜的合成及其抗生育活性的探索

The synthesis of curcumene sesquiterpenes and the exploration of their antiferetility effect

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【作者】 赵月琨陈锺瑛严秉淳

【Author】 Zhao Yuekun, Chen Zhongying Yan Bingchun (Department of Fine Chemicals)

【机构】 华东化工学院精细化工系华东化工学院精细化工系

【摘要】 对姜黄烯类倍半萜进行了研究。全合成得到(±)α-姜黄烯、(±)β-姜黄烯,脱氢-α-姜黄烯三个倍半萜类化合物。经药理初筛,表明都具有一定的抗早孕生物活性,还探索了倍半萜姜烯的合成,由6-(4′-甲氧基-1′,4′-环己二烯)-2-甲基-2-庚烯经酸性水解得重要中间体6-(4′-羰基-1′-环己烯)-2-甲基-2-庚烯(姜烯酮)。经光谱解析,确证在所用酸性水解条件下,β,γ-碳碳双键并不随同转位。这与甾体合成中,相应的酸性水解反应不同。

【Abstract】 The synthesis of curcumene sesquiterpenes—(±) a-curcumene, (±)β-curcurnene and dehydro-a-curcumene—is described. These three curcumene analogs are endowed with antifertility effect to a certain extent indicated by preliminary pharmaeological test.The synthesis of zingiberone, the key intcrmcdiate of zingiberene, is also described. The author found that in contrast with the acid hydrolysis of β,γ-unsaturated enol ether in steroid chemistry, the enol ether group of the precursor, 6-(4′-methoxy-1′,4′-cyclo-hexdienyl)-2-methyl-2-heptene, was transformed into carbonyl group without the accompanying isomerization of β,γ-double bond under the appropriate condition of acid hydrolysis.

【基金】 中国科学院科学基金资助的课题
  • 【被引频次】8
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