(1S,3R,6R,8S,9R,10R)-6-(4-methoxyphenyl)-2,5,7,11-tetraoxatricyclo[8.5.0.03,8]pentadec-13-en-9-ol | 440320-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,3R,6R,8S,9R,10R)-6-(4-methoxyphenyl)-2,5,7,11-tetraoxatricyclo[8.5.0.03,8]pentadec-13-en-9-ol
• CAS: 440320-29-6
• 化学式: C₁₈H₂₂O₆
• 分子量: 334.369
• InChiKey: KBBGHVMZEWRCAO-PYTCMNEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,3R,6R,8S,9R,10R)-6-(4-methoxyphenyl)-2,5,7,11-tetraoxatricyclo[8.5.0.03,8]pentadec-13-en-9-ol 在 palladium diacetate 吡啶 、 咪唑 、 三乙基硅烷 、 lithium hydroxide 、 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 2,6-二叔丁基-4-甲基吡啶 、 三乙基硼 、 三丁基膦 、 三氟甲磺酸三甲基硅酯 、 三(三甲基硅基)硅烷 、 4 A molecular sieve 、 氢氟酸 、 碘 、 三甲基铝 、 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 sodium hydride 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 四氯化碳 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 165.34h， 生成
  参考文献：
  名称：

  Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using O,S-Acetals As Key Intermediates

  摘要：

  [GRAPHICS]Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.

  DOI：

  10.1021/ol062350h
• 作为产物：
  描述：

  3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene 在 Grubbs catalyst first generation 、 氨 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (1S,3R,6R,8S,9R,10R)-6-(4-methoxyphenyl)-2,5,7,11-tetraoxatricyclo[8.5.0.03,8]pentadec-13-en-9-ol
  参考文献：
  名称：

  Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C

  摘要：

  Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00041-8

文献信息

• Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C
  作者：Shoji Kobayashi、Yusuke Takahashi、Kazuo Komano、Babak H. Alizadeh、Yuuya Kawada、Tohru Oishi、Shin-ichiro Tanaka、Yoshihiro Ogasawara、Shin-ya Sasaki、Masahiro Hirama

  DOI：10.1016/j.tet.2004.07.010

  日期：2004.9

  The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of the left wing of Caribbean ciguatoxin
  作者：Shuji Yamashita、Ryohei Uematsu、Masahiro Hirama

  DOI：10.1016/j.tet.2011.05.080

  日期：2011.9

  Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are potent toxic polycyclic ethers. In this paper, we report a stereoselective and secure route to the left wing of Caribbean ciguatoxin on the basis of a 6-exo radical cyclization strategy. (C) 2011 Elsevier Ltd. All rights reserved.
• Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using <i>O</i>,<i>S</i>-Acetals As Key Intermediates
  作者：Masayuki Inoue、Shuji Yamashita、Yuuki Ishihara、Masahiro Hirama

  DOI：10.1021/ol062350h

  日期：2006.12.1

  [GRAPHICS]Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.
• Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C
  作者：Megumi Maruyama、Masayuki Inoue、Tohru Oishi、Hiroki Oguri、Yoshihiro Ogasawara、Yumi Shindo、Masahiro Hirama

  DOI：10.1016/s0040-4020(02)00041-8

  日期：2002.3

  Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis. (C) 2002 Elsevier Science Ltd. All rights reserved.