isocostus lactone | 38236-17-8

• 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: isocostus lactone
• 英文别名: (3S,3aS,6aR,9aR,9bS)-3,9-dimethyl-6-methylidene-3,3a,4,5,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• CAS: 38236-17-8
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: GAXXKXAIPLVKGB-PEDHHIEDSA-N

物化性质

• 沸点：
  377.2±41.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  isocostus lactone 在 sodium tetrahydroborate 、 W-2 Raney Ni 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 (-)-compressanolide
  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：

  山道年 在 吡啶 、 potassium acetate 、 lithium carbonate 、 potassium carbonate 、 溶剂黄146 、 lithium bromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 isocostus lactone
  参考文献：
  名称：

  Studies on the syntheses of sesquiterpene lactones. 11. The syntheses of 3-epizaluzanin C, zaluzanin C, zaluzanin D, and related compounds 3.alpha.-hydroxyguaia-1(10),4(15),11(13)-trieno-12,6.alpha.-lactone and 3.alpha.-hydroxyguaia-4(15),9,11(13)-trieno-12,6.alpha.-lactone

  摘要：

  DOI：

  10.1021/jo00269a039

文献信息

• Total Syntheses of Ainsliadimer B and Gochnatiolides A and B
  作者：Dongliang Xia、Yu Du、Zhi Yi、Hao Song、Yong Qin

  DOI：10.1002/chem.201204292

  日期：2013.4.2

  syntheses of ainsliadimer B and gochnatiolides A and B from α‐santonin have been accomplished in 25 steps with approximately 1 % overall yield. A Diels–Alder reaction of natural dehydrozaluzanin C with a monomeric guaianolide derivative allows stereoselective assembly of a dimeric gochnatiolide‐type skeleton with the required stereochemistry and preinstalled functionalities for the synthesis of dimeric

  噢，我的天哪：用25个步骤完成了α-桑顿酸合成ainsliadimer B和gochnatiolide A和B的总产率约为1％。天然脱氢zaluzanin C与单体愈创木酚内酯衍生物的Diels-Alder反应可以立体选择性地组装二聚体gochnatiolide型骨架，并具有所需的立体化学和用于合成二聚体insinadimer B和gochnatiolides A和B的预装功能（参见方案）。
• Synthesis (in ent-form) of a novel jalcaguaianolide from Ferula arrigonii Bocchieri
  作者：Philippe Delair、Nina Kann、Andrew E. Greene

  DOI：10.1039/p19940001651

  日期：——

  A recently isolated isodehydrocostus lactone from the genus Ferula(Umbelliferae) has been stereoselectively prepared in ent-form from α-santonin by photochemical transformation to O-acetylisophotosantonic lactone followed by functional group manipulations that conclude with a one-step γ-butyrolactone →Δα,β-butenolide conversion; the synthesis corroborates both the structure and the relative and absolute

  从该属甲最近分离isodehydrocostus内酯阿魏（伞形科植物）已得到立体选择性地制备ENT -形式从α-山道年通过光化学转化为ö -acetylisophotosaNTonic内酯，随后，与一步法γ丁内酯→Δ结束官能团操作α ，β-丁烯内酯转化；合成证实了天然产物的结构以及相对和绝对立体化学。
• TOTAL SYNTHESES OF ZALUZANIN C, ZALUZANIN D, AND 3-EPIZALUZANIN C
  作者：Masayoshi Ando、Hiroaki Yamaoka、Kahei Takase

  DOI：10.1246/cl.1982.501

  日期：1982.4.5

  The biologically active guaianolides, zaluzanin C and zaluzanin D, and the stereoisomeric guaianolide, 3-epizaluzanin C, have been synthesized by two different procedures. The stereochemistry at C3 of zaluzanin C has been established to be S configuration by this synthesis.

  通过两种不同的程序合成了具有生物活性的愈创木酚内酯--扎鲁扎宁 C 和扎鲁扎宁 D，以及立体异构愈创木酚内酯--3-表扎鲁扎宁 C。通过这种合成方法，确定了扎鲁扎宁 C C3 的立体化学结构为 S 构型。
• 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.