(12S)-12-acetoxy-15,16-epoxylabda-7,13(16),14-triene | 434284-21-6

• 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: (12S)-12-acetoxy-15,16-epoxylabda-7,13(16),14-triene
• 英文别名: [(1S)-2-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-1-(furan-3-yl)ethyl] acetate
• CAS: 434284-21-6
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: JQPHEXBZJLFBIP-BPBCIEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (12S)-12-acetoxy-15,16-epoxylabda-7,13(16),14-triene 在 吡啶 、 air 、 rose bengal 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (12S)-12,15-diacetoxylabda-7,14-dien-16,15-olide
  参考文献：
  名称：

  An Approach to Furolabdanes and Their Photooxidation Derivatives from R-(+)-Sclareolide

  摘要：

  A synthetic route to furolabdanes from commercially available R-(+)-selareolide is reported, with the specific aim of preparing (12R and 12S,15xi)-12,15-dihydroxylabda-7,13-dien-16,15-olides (3 and 5) and (12R and 12S,16xi)-12,16-dihydroxylabda-7,13-dien-15,16-olides (4 and 6). The key points of our approach are the use of Weinreb's amide 11 to join the furan ring to the terpenic unit. Photooxidation of the furan moiety of compounds 15 and 16, and of their acetates 19 and 20, has been used to built the hydroxybutenolide fragment. In this way the four possible isomers at the butenolide moiety, compounds 3-6, and their C-12 acetyl derivatives 21-24 have been obtained. On the basis of comparison of the spectral data (H-1 NMR) of the synthetic peracetates 25-28 (derived from 21-24) with the reported data for the peracetate 2 (derived from the natural product 1), the relative configuration at carbon C-12 of the natural product has been corrected. Furthermore, the absolute configuration of the natural product 1, considered to belong to the enantio-series, has to be changed to the normal-series on the basis of the optical rotation obtained for the synthetic derivative.

  DOI：

  10.1021/np010590u
• 作为产物：
  描述：

  N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide 在 吡啶 、 正丁基锂 、 cerium(III) chloride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 61.0h， 生成 (12S)-12-acetoxy-15,16-epoxylabda-7,13(16),14-triene
  参考文献：
  名称：

  An Approach to Furolabdanes and Their Photooxidation Derivatives from R-(+)-Sclareolide

  摘要：

  A synthetic route to furolabdanes from commercially available R-(+)-selareolide is reported, with the specific aim of preparing (12R and 12S,15xi)-12,15-dihydroxylabda-7,13-dien-16,15-olides (3 and 5) and (12R and 12S,16xi)-12,16-dihydroxylabda-7,13-dien-15,16-olides (4 and 6). The key points of our approach are the use of Weinreb's amide 11 to join the furan ring to the terpenic unit. Photooxidation of the furan moiety of compounds 15 and 16, and of their acetates 19 and 20, has been used to built the hydroxybutenolide fragment. In this way the four possible isomers at the butenolide moiety, compounds 3-6, and their C-12 acetyl derivatives 21-24 have been obtained. On the basis of comparison of the spectral data (H-1 NMR) of the synthetic peracetates 25-28 (derived from 21-24) with the reported data for the peracetate 2 (derived from the natural product 1), the relative configuration at carbon C-12 of the natural product has been corrected. Furthermore, the absolute configuration of the natural product 1, considered to belong to the enantio-series, has to be changed to the normal-series on the basis of the optical rotation obtained for the synthetic derivative.

  DOI：

  10.1021/np010590u

文献信息

• An Approach to Furolabdanes and Their Photooxidation Derivatives from <i>R</i>-(+)<i>-</i>Sclareolide
  作者：María C. de la Torre、Isabel García、Miguel A. Sierra

  DOI：10.1021/np010590u

  日期：2002.5.1

  A synthetic route to furolabdanes from commercially available R-(+)-selareolide is reported, with the specific aim of preparing (12R and 12S,15xi)-12,15-dihydroxylabda-7,13-dien-16,15-olides (3 and 5) and (12R and 12S,16xi)-12,16-dihydroxylabda-7,13-dien-15,16-olides (4 and 6). The key points of our approach are the use of Weinreb's amide 11 to join the furan ring to the terpenic unit. Photooxidation of the furan moiety of compounds 15 and 16, and of their acetates 19 and 20, has been used to built the hydroxybutenolide fragment. In this way the four possible isomers at the butenolide moiety, compounds 3-6, and their C-12 acetyl derivatives 21-24 have been obtained. On the basis of comparison of the spectral data (H-1 NMR) of the synthetic peracetates 25-28 (derived from 21-24) with the reported data for the peracetate 2 (derived from the natural product 1), the relative configuration at carbon C-12 of the natural product has been corrected. Furthermore, the absolute configuration of the natural product 1, considered to belong to the enantio-series, has to be changed to the normal-series on the basis of the optical rotation obtained for the synthetic derivative.