| 1003193-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• CAS: 1003193-18-7
• 化学式: C₉H₁₆N₆O₂
• 分子量: 240.265
• InChiKey: NIPCOUHXWDVEAS-ILCAFMNSSA-N

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Decarbamoyloxysaxitoxin and (+)-Saxitoxin

  摘要：

  AbstractPlaying the sax: The enantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) are reported. A new methodology was developed for the synthesis of STXs, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine.magnified imageEnantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) were achieved. The characteristic spiro‐fused cyclic guanidine structure of STX was constructed by oxidation at the C4 position with IBX via an α‐iminium carbonyl intermediate and acid‐promoted cyclization of guanidine at the C5 position. A second‐generation methodology was developed for the synthesis of STX, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine. This approach provides efficient access to the key diamine intermediate for STXs.

  DOI：

  10.1002/asia.200800382
• 作为产物：
  描述：

  在 Pearlman's catalist 、 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Decarbamoyloxysaxitoxin and (+)-Saxitoxin

  摘要：

  AbstractPlaying the sax: The enantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) are reported. A new methodology was developed for the synthesis of STXs, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine.magnified imageEnantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) were achieved. The characteristic spiro‐fused cyclic guanidine structure of STX was constructed by oxidation at the C4 position with IBX via an α‐iminium carbonyl intermediate and acid‐promoted cyclization of guanidine at the C5 position. A second‐generation methodology was developed for the synthesis of STX, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine. This approach provides efficient access to the key diamine intermediate for STXs.

  DOI：

  10.1002/asia.200800382

文献信息

• Total Synthesis of (−)-Decarbamoyloxysaxitoxin
  作者：Osamu Iwamoto、Hiroyuki Koshino、Daisuke Hashizume、Kazuo Nagasawa

  DOI：10.1002/anie.200703326

  日期：2007.11.19