(-)-boehmeriasin A | 666175-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (-)-boehmeriasin A
• 英文别名: (R)-boehmeriasin A；boehmeriasin A；(14aR)-3,6,7-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine
• CAS: 666175-37-7
• 化学式: C₂₄H₂₇NO₃
• 分子量: 377.483
• InChiKey: ANTGAFQZQJMDNP-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-7-(3,4-dimethoxyphenyl)-8-(4-methoxyphenyl)-2,3,4,6,9,9a-hexahydro-1H-quinolizine 在 三氟代氧化钒(V) 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.0h， 以92%的产率得到(-)-boehmeriasin A
  参考文献：
  名称：

  通过有机催化分子内 Aza-Michael 加成对映选择性合成 Cryptopleurine 和 Boehmeriasin A

  摘要：

  从市售的 Cbz 保护的 2-哌啶酮中分 8 个步骤实现菲喹唑啉生物碱隐胸苷和勃姆虫素 A 的对映选择性合成，总产率分别为 22% 和 20%。该路线的关键步骤是分子内对映选择性氮杂-迈克尔加成、分子内醛醇加成和氧化偶联。

  DOI：

  10.1055/s-0031-1290457

文献信息

• First Asymmetric Synthesis of Boehmeriasin A
  作者：David Dumoulin、Stéphane Lebrun、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1002/ejoc.200901404

  日期：2010.4

  The first asymmetric synthesis of phenanthroquinolizidine alkaloid (R)-boehmeriasin A is described. Two alternative synthetic pathways to the key intermediate (RS,R)-4 were achieved through a combination of highly diastereoselective 1,2-nucleophilic addition on (―)-(S)-1-amino-2-(methoxymethyl)pyrrolidine hydrazones with a ring-closing metathesis to ensure the construction of the piperidine template

  描述了菲喹唑啶生物碱 (R)-勃姆菌素 A 的第一个不对称合成。通过对 (-)-(S)-1-氨基-2-(甲氧基甲基)吡咯烷腙进行高度非对映选择性的 1,2-亲核加成与闭环复分解，以确保哌啶模板的构建。随后的酰化/氧化/羟醛缩合/自由基环化序列完成了标题 (R) 配置的天然产物的组装。
• Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2
  作者：Michael S. Christodoulou、Francesco Calogero、Marcus Baumann、Aída Nelly García-Argáez、Stefano Pieraccini、Maurizio Sironi、Federico Dapiaggi、Raffaella Bucci、Gianluigi Broggini、Silvia Gazzola、Sandra Liekens、Alessandra Silvani、Maija Lahtela-Kakkonen、Nadine Martinet、Alfons Nonell-Canals、Eduardo Santamaría-Navarro、Ian R. Baxendale、Lisa Dalla Via、Daniele Passarella

  DOI：10.1016/j.ejmech.2015.01.038

  日期：2015.3

  Two synthetic approaches to boehmeriasin A are described. A gram scale racemic preparation is accompanied by an efficient preparation of both the pure enantiomers using the conformationally stable 2-piperidin-2-yl acetaldehyde as starting material. The anti-proliferative activity in three cancer cell lines (CEM, HeLa and L1210) and two endothelial cell lines (HMEC-1, BAEC) indicates promising activity at the nanomolar range. Topoisomerases and SIRT2 are identified as biological targets and the experimental data has been supported by docking studies. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation
  作者：Ziwen Wang、Qingmin Wang

  DOI：10.1016/j.tetlet.2009.12.135

  日期：2010.3

  A concise and efficient route involving Parham-type cycliacylation as the key step has been used to synthesize phenanthroquinolizidine alkaloids 1a-c and 2a-c. Among the products, 1b-(S), 1b-(R), 2a-(14S,15S), 2a-(14aR,15R), and 2b were synthesized for the first time. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of Cryptopleurine and Boehmeriasin A via ­Organocatalytic Intramolecular Aza-Michael Addition
  作者：Shouyun Yu、Chuanqi Zeng、Hanbin Liu、Mengyao Zhang、Jiajia Guo、Shunchao Jiang

  DOI：10.1055/s-0031-1290457

  日期：——

  The enantioselective synthesis of phenanthroquinolizidine alkaloids cryptopleurine and boehmeriasin A was achieved in eight steps from commercial available Cbz-protected 2-piperidinone in 22% and 20% overall yield, respectively. The key steps of this route are intramolecular enantioselective aza-Michael addition, intramolecular aldol addition, and oxidative coupling.

  从市售的 Cbz 保护的 2-哌啶酮中分 8 个步骤实现菲喹唑啉生物碱隐胸苷和勃姆虫素 A 的对映选择性合成，总产率分别为 22% 和 20%。该路线的关键步骤是分子内对映选择性氮杂-迈克尔加成、分子内醛醇加成和氧化偶联。