CONSTITUENTS OF WITHANIA SOMNIFERA DUN .3. SIDE CHAIN OF WITHAFERIN A
CONSTITUENTS OF WITHANIA SOMNIFERA DUN .3. SIDE CHAIN OF WITHAFERIN A
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DOI：
10.1021/jo01017a015
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发表时间：
1965-01-01
影响因子：
3.6
通讯作者：
SHVO, Y
中科院分区：
文献类型：
--
作者：
LAVIE, D;GLOTTER, E;SHVO, Y
新证据表明，含双酚的洋红素 B (la) 的氢化通过氢的 1, 4-加成生成四氢异洋红素 B (3-羟基-2-酮)，而乙酰氧基衍生物 (II) 通过 1, 2-加成生成 2-乙酰氧基-3-酮产物 (III)。葫芦素，即 elatericin B (la) 和 elaterin (lb) 据报道，第一摩尔氢被消耗在侧链双键的还原中，而第二摩尔氢则还原环 A 中二异酚体系的烯醇双键。 4 预期产物与二氢 elatericin A (VII) 或二氢葫芦素 B (23, 24-二氢) 相同VIb) 应形成。然而，得到了不同的化合物。这种差异可以通过涉及 C-2 不对称中心的差向异构体的形成来解释。
New evidence shows that the hydrogenation of the diosphenol-containing elatericin B (la) proceeds through a 1, 4-addition of hydrogen to yield tetrahydroisoelatericin B (3-hydroxy-2-one), whereas the acetoxyderivative (II) proceeds through a 1, 2-addition yielding a 2-acetoxy-3-one product (III).In previous papers dealing with the hydrogenation of the diosphenol-containing cucurbitacins, namely elatericin B (la) and elaterin (lb) it has been reported that the first mole of hydrogen was consumed in the reduc-tion of the doublebond on the side chain, whereas the second reduced the enolic double bond of the dios-phenol system in ring A. 4 It was expected that prod-ucts identical with dihydroelatericin A (VII) or dihydrocucurbitacin B (23, 24-dihydro VIb) should form. However, different compounds were obtained. The difference was explained in terms of the formation of epimers involving the center of asymmetry at C-2.