(5α,9α,10β,14α)-(-)-13-(Hydroxymethyl)-17-norkaur-15-en-14-ol | 143970-49-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (5α,9α,10β,14α)-(-)-13-(Hydroxymethyl)-17-norkaur-15-en-14-ol
• 英文别名: (1S,4S,9S,10R,13S,16R)-13-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-14-en-16-ol
• CAS: 143970-49-4
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: OEPVEVQWONUJQW-MCHXDPIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  <3S/R-(3α/β,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 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以67%的产率得到(5α,9α,10β,14α)-(-)-13-(Hydroxymethyl)-17-norkaur-15-en-14-ol
  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