(+)-4-deoxygigantecin | 143572-82-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-4-deoxygigantecin
• 英文别名: (2S)-4-[7-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]heptyl]-2-methyl-2H-furan-5-one
• CAS: 143572-82-1
• 化学式: C₃₇H₆₆O₇
• 分子量: 622.927
• InChiKey: AUIKUKHBIJHVLQ-QMSPDADRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  44
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-4-deoxygigantecin 在 吡啶 、 4-二甲氨基吡啶 、 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 56.0h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-[(2R,5R)-5-((4R,7S)-7-{(2S,5R)-5-[7-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-heptyl]-tetrahydro-furan-2-yl}-[1,3]dioxepan-4-yl)-tetrahydro-furan-2-yl]-tridecyl ester
  参考文献：
  名称：

  (2,4-cis and trans)-Gigantecinone and 4-Deoxygigantecin, Bioactive Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenins, from Goniothalamus giganteus

  摘要：

  Two new acetogenins, (2,4-cis and trans)-gigantecinone (1), isolated as a mixture, and 4-deoxygigantecin (2), a known acetogenin whose absolute stereochemistry has not been determined previously, were isolated using activity-directed fractionation, from the bark of Goniothalamus giganteus. A key step in solving their absolute stereochemistries was the preparation of 1,4-diol formaldehyde acetal derivatives (1b and 2a). Using the advanced Mosher ester method and circular dichroism, the absolute stereochemistries of I and 2 were revealed and were found to be the same as that of gigantecin (3), which supports a common biogenetic origin. Both 1 and Ib showed potent and selective cytotoxicities against the PC-3 human prostate adenocarcinoma cell line. Against yellow fever mosquito larvae, 1 and 2 were more potent than rotenone in pesticidal activity. Longimicin C and a mixture of (2,4-cis and trans)-isoannonacin were also isolated for the first time from this species.

  DOI：

  10.1021/np970211q
• 作为产物：
  描述：

  (S)-3-(2'-formylethyl)-5-methyl-2,5-dihydrofuran-2-one 在 Wilkinson's catalyst chromium dichloride 、 copper(l) iodide 、 四(三苯基膦)钯 、 二甲基硫 、 三氟化硼乙醚 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 (+)-4-deoxygigantecin
  参考文献：
  名称：

  Total synthesis of (+)-4-deoxygigantecin

  摘要：

  将(+)-4-去氧巨豆三烯素(1)从光学纯的(-)-muricatacin(3)中进行全合成。具体来说，3通过一个五步反应体系生成关键中间体5，然后通过双四氢呋喃单元1 1的形成和与碘代内酯合成体1 6的偶联反应，转化为(+)-4-去氧巨豆三烯素(1)。(C)1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00856-3

文献信息

• Total synthesis of (+)-4-deoxygigantecin
  作者：Hidefumi Makabe、Akira Tanaka、Takayuki Oritani

  DOI：10.1016/s0040-4039(97)00856-3

  日期：1997.6

  (+)-4-Deoxygigantecin (1) was totally synthesized from enantiomerically pure (-)-muricatacin (3). Thus, 3 afforded the key intermediate 5 through a five-step reaction sequence, which was then converted to (+)-4-deoxygigantecin (1) via the formation of bis-tetrahydrofuran unit 1 1 and a coupling reaction with iodo lactone synthon 1 6. (C) 1997 Elsevier Science Ltd.

  将(+)-4-去氧巨豆三烯素(1)从光学纯的(-)-muricatacin(3)中进行全合成。具体来说，3通过一个五步反应体系生成关键中间体5，然后通过双四氢呋喃单元1 1的形成和与碘代内酯合成体1 6的偶联反应，转化为(+)-4-去氧巨豆三烯素(1)。(C)1997 Elsevier Science Ltd.
• (2,4-<i>cis</i> and <i>trans</i>)-Gigantecinone and 4-Deoxygigantecin, Bioactive Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenins, from <i>Goniothalamus giganteus</i>
  作者：Feras Q. Alali、Yan Zhang、Lingling Rogers、J. L. McLaughlin

  DOI：10.1021/np970211q

  日期：1997.9.1

  Two new acetogenins, (2,4-cis and trans)-gigantecinone (1), isolated as a mixture, and 4-deoxygigantecin (2), a known acetogenin whose absolute stereochemistry has not been determined previously, were isolated using activity-directed fractionation, from the bark of Goniothalamus giganteus. A key step in solving their absolute stereochemistries was the preparation of 1,4-diol formaldehyde acetal derivatives (1b and 2a). Using the advanced Mosher ester method and circular dichroism, the absolute stereochemistries of I and 2 were revealed and were found to be the same as that of gigantecin (3), which supports a common biogenetic origin. Both 1 and Ib showed potent and selective cytotoxicities against the PC-3 human prostate adenocarcinoma cell line. Against yellow fever mosquito larvae, 1 and 2 were more potent than rotenone in pesticidal activity. Longimicin C and a mixture of (2,4-cis and trans)-isoannonacin were also isolated for the first time from this species.