(2R,4E,6E,10S,11S,12E,14S,18E)-11,14-dihydroxy-4-methyl-2-{(2R,3E,5E)-4-methyl-6-[(3-methylbut-2-enoyl)amino]hexa-3,5-dien-2-yl}-20-oxooxacycloicosa-4,6,12,18-tetraen-10-yl carbamate | 863116-48-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (2R,4E,6E,10S,11S,12E,14S,18E)-11,14-dihydroxy-4-methyl-2-{(2R,3E,5E)-4-methyl-6-[(3-methylbut-2-enoyl)amino]hexa-3,5-dien-2-yl}-20-oxooxacycloicosa-4,6,12,18-tetraen-10-yl carbamate
• 英文别名: (-)-palmerolide A；palmerolide A；[(2R,4E,6E,10S,11S,12E,14S,18E)-11,14-dihydroxy-4-methyl-2-[(2R,3E,5E)-4-methyl-6-(3-methylbut-2-enoylamino)hexa-3,5-dien-2-yl]-20-oxo-1-oxacycloicosa-4,6,12,18-tetraen-10-yl] carbamate
• CAS: 863116-48-7
• 化学式: C₃₃H₄₈N₂O₇
• 分子量: 584.753
• InChiKey: HEOKDDVDVGNHMR-DAUCKHFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  148
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,4E,6E,10S,11S,12E,14S,18E)-4-methyl-2-((R,3E,5E)-4-methyl-6-(3-methylbut-2-enamido)hexa-3,5-dien-2-yl)-20-oxo-11,14-bis((triisopropylsilyl)oxy)oxacycloicosa-4,6,12,18-tetraen-10-yl carbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以100%的产率得到(2R,4E,6E,10S,11S,12E,14S,18E)-11,14-dihydroxy-4-methyl-2-{(2R,3E,5E)-4-methyl-6-[(3-methylbut-2-enoyl)amino]hexa-3,5-dien-2-yl}-20-oxooxacycloicosa-4,6,12,18-tetraen-10-yl carbamate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Palmerolide A via Organoboron Methodology

  摘要：

  A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could the way to the design of simplified analogues of palmerolide.

  DOI：

  10.1021/ja906429c

文献信息

• Total Synthesis of the Originally Proposed and Revised Structures of Palmerolide A and Isomers Thereof
  作者：K. C. Nicolaou、Ya-Ping Sun、Ramakrishna Guduru、Biswadip Banerji、David Y.-K. Chen

  DOI：10.1021/ja710485n

  日期：2008.3.1

  Palmerolide A is a recently disclosed marine natural product possessing striking biological properties, including potent and selective activity against the melanoma cancer cell line UACC-62. The total syntheses of five palmerolide A stereoisomers, including the originally proposed (1) and the revised [ent-(19-epi-20-epi-1)] structures, have been accomplished. The highly convergent and flexible strategy

  Palmerolide A 是最近公开的一种海洋天然产物，具有惊人的生物学特性，包括针对黑色素瘤癌细胞系 UACC-62 的有效和选择性活性。五种palmerolide A立体异构体的全合成，包括最初提出的(1)和修改后的[ent-(19-epi-20-epi-1)]结构，已经完成。为这些综合开发的高度收敛和灵活的策略涉及构建关键构建块 2、19-epi-2、20-epi-2、ent-2、3、ent-3、4 和 ent-4，以及它们的组装和细化目标化合物。对于构建单元的结合，采用了Stille偶联反应、Yamaguchi酯化、Horner-Wadsworth-Emmons烯化和闭环复分解反应，后者对于palmerolide结构的大环的立体选择性形成至关重要。还研究了 Horner-Wadsworth-Emmons 烯化和 Yamaguchi 内酯化，并发现作为构建 Palmerolide
• PALMEROLIDES: METHODS OF PREPARATION AND DERIVATIVES THEREOF
  申请人：DE BRABANDER Jef K.

  公开号：US20080249162A1

  公开（公告）日：2008-10-09

  Organic compounds having Formulas I and II are provided where the variables have the values described herein. Pharmaceutical formulations include the organic compounds or pharmaceutically acceptable salts thereof and a pharmaceutically acceptable carrier can be prepared. Methods of preparing the compounds includes deprotecting protected precursor compounds. Methods of treating cancer or inhibiting ATPase include administering the organic compounds to a subject in need thereof.

  提供具有化学式I和II的有机化合物，其中变量具有此处描述的值。药物配方包括该有机化合物或其药用可接受盐以及药用可接受载体可制备。制备该化合物的方法包括去保护受保护的前体化合物。治疗癌症或抑制ATP酶的方法包括将有机化合物用于需要的对象。
• Total Synthesis of the Originally Proposed and Revised Structures of Palmerolide A
  作者：K. C. Nicolaou、Ramakrishna Guduru、Ya-Ping Sun、Biswadip Banerji、David Y.-K. Chen

  DOI：10.1002/anie.200702243

  日期：2007.8.3
• US7838691B2
  申请人：——

  公开号：US7838691B2

  公开（公告）日：2010-11-23