(7R,8aR,10aR)-7-hydroxy-4-(methoxymethoxy)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-2-carbaldehyde | 1069118-57-5

• 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: (7R,8aR,10aR)-7-hydroxy-4-(methoxymethoxy)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-2-carbaldehyde
• CAS: 1069118-57-5
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: PZVGACXZRFHCPM-GPMSIDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (4-(3-methyl-2-butenyl)-3,5-bis(methoxymethoxy)benzyl)phosphonate 、 (7R,8aR,10aR)-7-hydroxy-4-(methoxymethoxy)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-2-carbaldehyde 在 15-冠醚-5 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,4aR,9aR)-tri(O-methoxymethyl)schweinfurthin G
  参考文献：
  名称：

  BF3 x Et2O 介导的级联环化：schweinfurthins F 和 G 的合成。

  摘要：

  天然二苯乙烯 (+)-schweinfurthin G (8) 的全合成已通过基于有效阳离子级联环化的序列完成。该级联过程由路易斯酸促进环氧化物的开环引发，并通过与作为其 MOM 醚“保护”的酚氧发生新反应而终止。已经检查了几种路易斯酸诱导这种新反应的能力，发现 BF3 x Et2O 是最有效的。在这些条件下唯一的主要副产物是预期的仲醇被发现为其 MOM 醚衍生物（例如，30）。虽然这种副产物可以通过水解转化为原始的目标化合物，它还可以用作受保护的醇，以允许在不使仲醇脱水的情况下制备苄基膦酸酯 (43)。所得的膦酸酯用于与代表目标化合物右半部分的醛的 Horner-Wadsworth-Emmons 缩合反应，这是对先前基于右半膦酸酯和左半醛缩合的研究的补充。

  DOI：

  10.1021/jo800951q
• 作为产物：
  描述：

  (2R,4aR,9aR)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,5-diol 在 水 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.17h， 生成 (7R,8aR,10aR)-7-hydroxy-4-(methoxymethoxy)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-2-carbaldehyde
  参考文献：
  名称：

  First total synthesis of (+)-vedelianin, a potent antiproliferative agent

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.01.137

文献信息

• Synthesis of Indole Analogues of the Natural Schweinfurthins
  作者：John G. Kodet、David F. Wiemer

  DOI：10.1021/jo4014244

  日期：2013.9.20

  An interest in the schweinfurthins, natural stilbenes with significant antiproliferative activity, has prompted efforts to prepare a set of indole analogues. To approach the desired compounds through a Horner-Wadsworth-Emmons condensation, new indole derivatives bearing a phosphonomethyl substituent in the B-ring were required. The parent indole system with the necessary substitution pattern was obtained through Stobbe condensation and cyclization. A prenyl substituent was incorporated at the C3 position of a 4,6-disubstituted indole through a highly regioselective electrophilic aromatic substitution reaction, while metalation and alkylation provided the C2-prenylated indole. After introduction of the phosphonate group through classical reactions, the new indole phosphonates were found to undergo the desired condensation with nonracemic aldehydes representing the schweinfurthin left half. This approach provides facile access to new heteroaromatic analogues of the natural schweinfurthins and should be applicable to many other natural stilbenes as well.
• Relevance of the C-5 position to schweinfurthin induced cytotoxicity
  作者：Joseph J. Topczewski、Michael P. Callahan、John G. Kodet、Jery D. Inbarasu、Nolan R. Mente、John A. Beutler、David F. Wiemer

  DOI：10.1016/j.bmc.2011.10.034

  日期：2011.12

  The schweinfurthins are an intriguing group of anti-proliferative agents that display low nanomolar activities against several cell types, including the human-derived glioblastoma cell line SF-295, but have little impact on other cell lines even at micromolar concentrations. This activity has inspired the synthesis of seven of the natural schweinfurthins, all with the correct absolute stereochemistry, and a variety of analogues designed to probe different facets of the pharmacophore. Reported herein is the synthesis of several new schweinfurthin analogues varied at the C-5 position along with data on their biological activity in the NCI 60 cell-line assay. (C) 2011 Elsevier Ltd. All rights reserved.