(+/-)-erythrodiene

• 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: (+/-)-erythrodiene
• 英文别名: (5R,7R)-4,10-dimethylidene-7-propan-2-ylspiro[4.5]decane
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: WKUVNTPZIMJKBY-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (+/-)-erythrodiene 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 (1S,5R,6R,9R)-9-Isopropyl-spiro[4.5]decane-1,6-diol
  参考文献：
  名称：

  Erythrodiene: A new spirobicyclic sesquiterpene of a rare skeletal class from the caribbean gorgonian coral Erythropodium caribaeorum

  摘要：

  Erythrodiene (1), a new sesquiterpene hydrocarbon of a rare structural class, has been isolated from the encrusting Caribbean gorgonian coral Erythropodium caribaeorum. The structure of the new compound was assigned on the basis of spectral studies and through an X-ray analysis of a reduced ozonolysis product, the diol 2.

  DOI：

  10.1016/s0040-4039(00)79158-1
• 作为产物：
  描述：

  5-isopropyl-2-oxocyclohexanecarboxylic acid methyl ester 在 盐酸 、 水 、 potassium hydride 、 六甲基二硅氮烷 、 sodium iodide 、 mercury dichloride 、 lithium iodide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (+/-)-erythrodiene
  参考文献：
  名称：

  A stereoselective total synthesis of (±)-erythrodiene

  摘要：

  Erythrodiene, a unique spirobicyclic sesquiterpene hydrocarbon from the Caribbean gorgonian cord Erythropodium caribaeorum, has been synthesized from 4-isopropylcyclohexanol in 8-steps and approximately 16% overall yield. The synthesis features a stereoselective intramolecular carbomercuration reaction as the key step.

  DOI：

  10.1016/s0040-4039(00)61502-2

文献信息

• A simple total synthesis of (±)-spirojatamol and (±)-erythrodiene via intramolecular 1,3-dipolar cycloaddition
  作者：Yuji Tokunaga、Maki Yagihashi、Masataka Ihara、Keiichiro Fukumoto

  DOI：10.1039/c39950000955

  日期：——

  An efficient synthesis of spirobicyclic sesquiterpenes, (±)-spirojatamol 1 and (±)-erythrodiene 2, using an intramolecular 1,3-dipolar cycloaddition as the pivotal step is described.

  本文描述了一种利用分子内1,3-偶极环加成反应作为关键步骤，高效合成倍半萜螺旋双环化合物（±）-螺旋佳他醇1和（±）-红没药烯2的方法。
• Total synthesis of (±)-erythrodiene and (±)-spirojatamol
  作者：Fu Cheng、Dong-Sen Duan、Ye Zhang、Tian-Lu Zheng、Xiao-Yun Zhang、Shao-Hua Wang、Xue-Tao Xu、Dao-Yong Zhu

  DOI：10.1016/j.tetlet.2021.153291

  日期：2021.11

  achieved from cyclobutone and isobutyraldehyde through an 11-step synthetic route. During the work, a tandem Castro-Stephens coupling/1, 3-acyloxy shift/cyclization/semipinacol rearrangement sequence, which was developed recently by the same group, was used as the key step to build the crucial spirocyclic intermediate 5b.

  通过 11 步合成路线，从环丁酮和异丁醛中获得了一种独特的 (±)-erythrodiene 和 (±)-spirojatamol 合成策略。在这项工作中，由同一小组最近开发的串联 Castro-Stephens 偶联/1, 3-酰氧基转移/环化/半哌啶醇重排序列被用作构建关键的螺环中间体5b的关键步骤。
• Synthesis of (−)-Erythrodiene and (+)-7-Epispirojatamolvia Intramolecular Pd-Catalyzed Allylzincation
  作者：Wolfgang Oppolzer、Felix Flachsmann

  DOI：10.1002/1522-2675(20010228)84:2<416::aid-hlca416>3.0.co;2-k

  日期：2001.2.28

  Two spirobicyclic sesquiterpenoids, (-)-erythrodiene (1) and (+)-7-epispirojatamol (30),were synthesized in enantiomerically pure form via an intramolecular allylzincation process. The allylzinc species were formed in the presence of Et,Zn via transmetallation of a catalytically generated allylpalladium intermediate. Several Pd catalysts were tested for this transformation, and [Pd(OAc)(2)/Bu3P(1 equiv.) was found to be, by far, the most effective. Whereas the preparation of 1 involved allylzincation of a tethered terminal olefin. 30 was formed via a novel intramolecular allylzincation of a methyl ketone. Both reactions showed the same stereochemical preference. yielding the spirobicyclic products in 95:5 and 4:1 diastereoisomer ratios, respectively.