(3S,3aS,6R,6aR,9aR,9bS)-6-hydroxy-3,6,9-trimethyl-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2-one | 17946-95-1

• 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: (3S,3aS,6R,6aR,9aR,9bS)-6-hydroxy-3,6,9-trimethyl-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• CAS: 17946-95-1
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: CWACFPQPFUIHTR-MRWSCNBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,3aS,6R,6aR,9aR,9bS)-6-hydroxy-3,6,9-trimethyl-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2-one 在 吡啶 、 sodium tetrahydroborate 、 三氟甲磺酸酐 、 W-2 Raney Ni 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 4α-hydroxy-5α,6β,7α,11β-H-guaian-1(10)-en-6,12-olide
  参考文献：
  名称：

  Stereoselective Synthesis of (+)-11βH,13-Dihydroestafiatin, (+)-11βH,13-Dihydroludartin, (−)-Compressanolide, and (−)-11βH,13-Dihydromicheliolide from Santonin

  摘要：

  Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11betaH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11betaH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11betaH,13-dihydromicheliolide (7), respectively.

  DOI：

  10.1021/np020109f
• 作为产物：
  描述：

  3β-tetrahydro-O-acetylisophotosantonic lactone 在 吡啶 、 氢氧化钾 、 lithium carbonate 、 lithium bromide 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 13.5h， 生成 (3S,3aS,6R,6aR,9aR,9bS)-6-hydroxy-3,6,9-trimethyl-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2-one
  参考文献：
  名称：

  Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides

  摘要：

  The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10392-1

文献信息

• A Biomimetic Total Synthesis of (+)-Ainsliadimer A
  作者：Chao Li、Xueliang Yu、Xiaoguang Lei

  DOI：10.1021/ol101705j

  日期：2010.10.1

  A protecting group free and biomimetic total synthesis of (+)-ainsliadimer A has been accomplished in 14 steps from a-santonin. The synthesis relies on a hydrogen bonding promoted [4 + 2]-hetero-Diels-Alder dimerization to afford the key homodimer intermediate, which demonstrates the feasibility of using nonenzymatic conditions to achieve the proposed biosynthesis.
• Regio- and stereoselective oxyfunctionalization at C-1 and C-5 in sesquiterpene guaianolides
  作者：Victoria Bargues、Gonzalo Blay、Luz Cardona、Begoña García、JoséR. Pedro

  DOI：10.1016/s0040-4020(97)10392-1

  日期：1998.2

  The regio- and stereoselective functionalization at C-1 and C-5 positions in a guaiane skeleton by allylic hydroxylation are described The stereochemistry of the resulting compounds are identical to those of the majority of natural 1- and 5-hydroxy-guaianolides. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselective Synthesis of (+)-11<b>β</b><i>H</i>,13-Dihydroestafiatin, (+)-11<b>β</b><i>H</i>,13-Dihydroludartin, (−)-Compressanolide, and (−)-11<b>β</b><i>H</i>,13-Dihydromicheliolide from Santonin
  作者：Victoria Bargues、Gonzalo Blay、Luz Cardona、Begoña García、José R. Pedro

  DOI：10.1021/np020109f

  日期：2002.11.1

  Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11betaH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11betaH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11betaH,13-dihydromicheliolide (7), respectively.