(Z)-(3S,3aS,6R,8R,12aS)-3-Hydroxy-8-methoxymethoxy-6,10,12a-trimethyl-2,3,3a,5,6,7,8,9,12,12a-decahydro-1H-cyclopentacycloundecen-4-one | 875432-00-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-(3S,3aS,6R,8R,12aS)-3-Hydroxy-8-methoxymethoxy-6,10,12a-trimethyl-2,3,3a,5,6,7,8,9,12,12a-decahydro-1H-cyclopentacycloundecen-4-one
• CAS: 875432-00-1
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: CZPDQHIQRBDIEB-LKEKTLJMSA-N

反应信息

• 作为反应物：
  描述：

  (Z)-(3S,3aS,6R,8R,12aS)-3-Hydroxy-8-methoxymethoxy-6,10,12a-trimethyl-2,3,3a,5,6,7,8,9,12,12a-decahydro-1H-cyclopentacycloundecen-4-one 在 锂硼氢 、 二乙基甲氧基硼烷 作用下， 以 乙醚 为溶剂， 生成 (Z)-(1S,3aS,8R,10S,12R,12aS)-8-Methoxymethoxy-3a,6,10-trimethyl-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecene-1,12-diol 、 (Z)-(1S,3aS,8R,10S,12S,12aS)-8-Methoxymethoxy-3a,6,10-trimethyl-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecene-1,12-diol
  参考文献：
  名称：

  Stereospecific rearrangement of α-hydroxyepoxide: efficient approach to the trans-bicyclo[9.3.0]tetradecane core en route to clavulactone

  摘要：

  We document a synthetic route to trans-bicyclo[9.3.0]tetradecanes. The strategy is based oil a quantitative and stereospecific Lewis acid mediated rearrangement of alpha-hydroxyepoxide to beta-hydroxyketone, which paved the way for the synthesis of clavulactone and clavirolides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.021
• 作为产物：
  描述：

  (Z)-(1S,2S,4S,6R,11S,14S)-6-Methoxymethoxy-4,8,11-trimethyl-15-oxa-tricyclo[12.1.0.0^1,11]pentadec-8-en-2-ol 在 lithium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以100%的产率得到(Z)-(3S,3aS,6R,8R,12aS)-3-Hydroxy-8-methoxymethoxy-6,10,12a-trimethyl-2,3,3a,5,6,7,8,9,12,12a-decahydro-1H-cyclopentacycloundecen-4-one
  参考文献：
  名称：

  Stereospecific rearrangement of α-hydroxyepoxide: efficient approach to the trans-bicyclo[9.3.0]tetradecane core en route to clavulactone

  摘要：

  We document a synthetic route to trans-bicyclo[9.3.0]tetradecanes. The strategy is based oil a quantitative and stereospecific Lewis acid mediated rearrangement of alpha-hydroxyepoxide to beta-hydroxyketone, which paved the way for the synthesis of clavulactone and clavirolides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.021