(1R,3R,4R,5S,7R,11S,13R,15S,17R,20S,21R,23S)-7-[(E,3S)-3,4-bis(naphthalen-2-ylmethoxy)but-1-enyl]-4-(naphthalen-2-ylmethoxy)-21-prop-2-enyl-2,6,12,16,22-pentaoxapentacyclo[13.10.0.03,13.05,11.017,23]pentacosa-8,18,24-trien-20-ol | 676609-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,3R,4R,5S,7R,11S,13R,15S,17R,20S,21R,23S)-7-[(E,3S)-3,4-bis(naphthalen-2-ylmethoxy)but-1-enyl]-4-(naphthalen-2-ylmethoxy)-21-prop-2-enyl-2,6,12,16,22-pentaoxapentacyclo[13.10.0.03,13.05,11.017,23]pentacosa-8,18,24-trien-20-ol
• CAS: 676609-54-4
• 化学式: C₆₀H₆₀O₉
• 分子量: 925.131
• InChiKey: OEOKHTOAJXHKOR-BHLXVXGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  69
• 可旋转键数：
  14
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,5S,7R,11S,13R,15S,17R,20S,21R,23S)-7-[(E,3S)-3,4-bis(naphthalen-2-ylmethoxy)but-1-enyl]-4-(naphthalen-2-ylmethoxy)-21-prop-2-enyl-2,6,12,16,22-pentaoxapentacyclo[13.10.0.03,13.05,11.017,23]pentacosa-8,18,24-trien-20-ol 在 4-二甲氨基吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.58h， 生成
  参考文献：
  名称：

  Synthesis of the Fully Functionalized ABCDE Ring Moiety of Ciguatoxin

  摘要：

  A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and construction of the tetrahydrooxepin E ring using a novel alpha-chlorosulfide synthon.

  DOI：

  10.1021/ol0364475
• 作为产物：
  描述：

  (1R,3S,5R,10S,13R,15R,16R,17S,23S)-8,8-dimethyl-16-(naphthalen-2-ylmethoxy)-4,7,9,14,18,24-hexaoxapentacyclo[13.9.0.03,13.05,10.017,23]tetracosa-11,19-diene 在 吡啶 、 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 2,6-二甲基吡啶 、 盐酸 、 bis(triphenylphosphine)nickel(II) chloride 、 正丁基锂 、 2,6-二叔丁基-4-甲基吡啶 、 草酰氯 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 二氯乙基铝 、 四丁基碘化铵 、 sodium hydride 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 130.63h， 生成 (1R,3R,4R,5S,7R,11S,13R,15S,17R,20S,21R,23S)-7-[(E,3S)-3,4-bis(naphthalen-2-ylmethoxy)but-1-enyl]-4-(naphthalen-2-ylmethoxy)-21-prop-2-enyl-2,6,12,16,22-pentaoxapentacyclo[13.10.0.03,13.05,11.017,23]pentacosa-8,18,24-trien-20-ol
  参考文献：
  名称：

  Synthesis of the Fully Functionalized ABCDE Ring Moiety of Ciguatoxin

  摘要：

  A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and construction of the tetrahydrooxepin E ring using a novel alpha-chlorosulfide synthon.

  DOI：

  10.1021/ol0364475

文献信息

• Total Synthesis of Ciguatoxin and 51-HydroxyCTX3C
  作者：Masayuki Inoue、Keisuke Miyazaki、Yuuki Ishihara、Atsushi Tatami、Yuyu Ohnuma、Yuuya Kawada、Kazuo Komano、Shuji Yamashita、Nayoung Lee、Masahiro Hirama

  DOI：10.1021/ja063041p

  日期：2006.7.1

  Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers with the 13 ether rings ranging from five- to nine-membered. In this paper, we describe the total synthesis of the two most toxic members of the ciguatoxin family, ciguatoxin 1 and 51-hydroxyCTX3C 2, based on a unified synthetic strategy. The key features in our syntheses were (i) direct construction of the O,S-acetal from the corresponding left and right wing fragments (3, 4, 14); (ii) stereo- and chemoselective radical reaction of the alpha-oxyradical with pentafluorophenyl acrylate to achieve cyclization of the seven-membered G-ring; (iii) ring-closing metathesis reaction to build the nine-membered F-ring; and (iv) an efficient protective group strategy using the oxidatively removable 2-naphthylmethyl groups.
• METHOD OF SYNTHESIS OF CIGUATOXIN CTX1B AND COMPOUNDS USEFUL FOR THE SYNTHESIS OF CIGUATOXIN CTX1B
  申请人：Japan Science and Technology Agency

  公开号：EP1982988B1

  公开（公告）日：2014-06-04