(4aR,9aR)-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydroxanthen-2-one | 1263362-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (4aR,9aR)-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydroxanthen-2-one
• CAS: 1263362-11-3
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: FZMQPQQBAKOZEM-OXQOHEQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aR,9aR)-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydroxanthen-2-one 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 cerium(III) chloride heptahydrate 、 水 、 N-甲基吗啉氧化物 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 43.92h， 生成 (6R,7S,8aR,10aR)-6,7-dihydroxy-4-(methoxymethoxy)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-2-carbaldehyde
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

  DOI：

  10.1021/jo1022102
• 作为产物：
  描述：

  [3-Bromo-4-(phenylmethoxymethoxy)phenyl]methanol 在 manganese(IV) oxide 、 正丁基锂 、 四丙基高钌酸铵 、 四甲基乙二胺 、 三氟化硼乙醚 、 sodium hydride 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 hexanes 、 乙醚 、 二氯甲烷 、 mineral oil 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 108.55h， 生成 (4aR,9aR)-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydroxanthen-2-one
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

  DOI：

  10.1021/jo1022102

文献信息

• First total synthesis of (+)-vedelianin, a potent antiproliferative agent
  作者：Joseph J. Topczewski、David F. Wiemer

  DOI：10.1016/j.tetlet.2011.01.137

  日期：2011.4

  The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (25,3R,4aR,9aR)-isomer. (C) 2011 Elsevier Ltd. All rights reserved.