<3S-(3α,3aα,5aS,7aα,11aβ,11bα)>-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-3,3-(epoxymethano)-8,8,11a-trimethylcyclobutaphenanthrene | 144000-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: <3S-(3α,3aα,5aS,7aα,11aβ,11bα)>-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-3,3-(epoxymethano)-8,8,11a-trimethylcyclobutaphenanthrene
• 英文别名: [3S-(3α,3aα,5aS,7aα,11aβ,11bα)]-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-3,3-(epoxymethano)-8,8,11a-trimethylcyclobuta[j]phenanthrene；(1'S,2S,4'S,9'S,10'R,14'S)-5',5',9'-trimethylspiro[oxirane-2,13'-tetracyclo[8.6.0.01,14.04,9]hexadec-15-ene]
• CAS: 144000-08-8
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: QVBNOXIDOSVVDH-CJEFFJQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Δ⁸⁽¹⁴⁾-podocarpen-13-one 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 丙酮 为溶剂， 反应 17.5h， 生成 <3S-(3α,3aα,5aS,7aα,11aβ,11bα)>-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-3,3-(epoxymethano)-8,8,11a-trimethylcyclobutaphenanthrene
  参考文献：
  名称：

  Spongian pentacyclic diterpenes. Stereoselective synthesis of (-)-dendrillol-1

  摘要：

  A formal total synthesis of the spongian diterpene (-)-dendrillol-1 (3), through a consice approach that could be used for the synthesis of other pentacyclic spongian diterpenes, is reported. The synthesis is based on the intramolecular acetalization of an acid-dialdehyde 4, which is prepared from (+)-podocarp-8(14)-en-13-one (5) via a sequence of transformations involving (a) introduction of a latent dialdehyde unit on 5 by photochemical reaction with acetylene, (b) reductive carboxylation at C-13 of photoadduct 6 to obtain acid 18, and (c) elaboration of the dialdehyde moiety at C-8 and C-14 of 18 by ozonolysis. Several procedures that have been examined for the reductive carboxylation at C-13 of 6 are described. A simple three-step procedure to effect the conversion of a podocarp-8-en-13-one system into a C-17-functionalized beyerane compound is also reported.

  DOI：

  10.1021/jo00051a035

文献信息

• Spongian pentacyclic diterpenes. Stereoselective synthesis of (-)-dendrillol-1
  作者：Antonio Abad、Manuel Arno、Ana C. Cunat、M. Luisa Marin、Ramon J. Zaragoza

  DOI：10.1021/jo00051a035

  日期：1992.12

  A formal total synthesis of the spongian diterpene (-)-dendrillol-1 (3), through a consice approach that could be used for the synthesis of other pentacyclic spongian diterpenes, is reported. The synthesis is based on the intramolecular acetalization of an acid-dialdehyde 4, which is prepared from (+)-podocarp-8(14)-en-13-one (5) via a sequence of transformations involving (a) introduction of a latent dialdehyde unit on 5 by photochemical reaction with acetylene, (b) reductive carboxylation at C-13 of photoadduct 6 to obtain acid 18, and (c) elaboration of the dialdehyde moiety at C-8 and C-14 of 18 by ozonolysis. Several procedures that have been examined for the reductive carboxylation at C-13 of 6 are described. A simple three-step procedure to effect the conversion of a podocarp-8-en-13-one system into a C-17-functionalized beyerane compound is also reported.