(14S,17S,18S)-N-((3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-14,17,18-trihydroxyoctacosanamide | 949463-70-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (14S,17S,18S)-N-((3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-14,17,18-trihydroxyoctacosanamide
• 英文别名: (14S,17S,18S)-N-((3S,11bS)-9,11-bis(benzyloxy)-2,3,4,6,7,11b-hexahydro-4-oxo-1H-pyrido[2,1-a]isoquinolin-3-yl)-14,17,18-trihydroxyoctacosanamide；(14S,17S,18S)-N-[(3S,11bS)-4-oxo-9,11-bis(phenylmethoxy)-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-3-yl]-14,17,18-trihydroxyoctacosanamide
• CAS: 949463-70-1
• 化学式: C₅₅H₈₂N₂O₇
• 分子量: 883.265
• InChiKey: FAJKHSSJDWCFRL-CODSXAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  64
• 可旋转键数：
  33
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (14S,17S,18S)-N-((3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-14,17,18-trihydroxyoctacosanamide 在 三氧化硫吡啶 、 sodium hydroxide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 10.0h， 以69%的产率得到(-)-schulzeine B
  参考文献：
  名称：

  海洋天然产物schulzeines B和C的C 28脂肪酸链的新方法：（-）-schulzeine B的简明非对映选择性全合成

  摘要：

  基于1-酒石酸衍生的C 4 chiron 11，通过连续的1，4-双链延长反应和催化不对称氢化作用，建立了对海洋天然产物舒尔西汀B和C的C 28脂肪酸链的对映选择性方法。手性三环核芯8是通过l-谷氨酸衍生的前体13的非对映选择性Pictet-Spengler环化反应（dr  = 89:11）构建的。在此基础上，公开了简明的（-）-舒尔西汀B（5）的全合成。

  DOI：

  10.1016/j.tet.2011.06.023
• 作为产物：
  描述：

  Z-L-GluOMe 在 palladium on activated charcoal 盐酸 、 三甲基氯硅烷 、 氢气 、 四丁基碘化铵 、 sodium cyanoborohydride 、 碳酸氢钠 、 caesium carbonate 、 溶剂黄146 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium iodide 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 47.5h， 生成 (14S,17S,18S)-N-((3S,11bS)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-14,17,18-trihydroxyoctacosanamide
  参考文献：
  名称：

  Total Syntheses of Schulzeines B and C

  摘要：

  Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihy-droxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.

  DOI：

  10.1021/jo070560h

文献信息

• Formal synthesis of schulzeines B and C
  作者：Punlop Kuntiyong、Sunisa Akkarasamiyo、Nuanpan Piboonsrinakara、Chitlada Hemmara、Poramate Songthammawat

  DOI：10.1016/j.tet.2011.07.085

  日期：2011.10

  A formal synthesis of schulzeines B and C, marine natural products with inhibitory effect against α-glucosidase, has been achieved. The key reactions of the synthesis are N-acyliminium ion cyclization, Sharpless asymmetric dihydroxylation, olefin cross metathesis, and asymmetric allylboration.

  已经完成了具有舒张作用的B和C的合成，这是一种对α-葡萄糖苷酶具有抑制作用的海洋天然产物。合成的关键反应是N-酰基亚胺离子环化，Sharpless不对称二羟基化，烯烃交叉复分解和不对称烯丙基硼化。
• Bowen, Edward G.; Wardrop, Duncan J., Journal of the American Chemical Society, 2009, vol. 131, p. 6062 - 6063
  作者：Bowen, Edward G.、Wardrop, Duncan J.

  DOI：——

  日期：——
• Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde
  作者：Gang Liu、Daniel Romo

  DOI：10.1021/ol802992m

  日期：2009.3.5

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.
• Total Syntheses of Schulzeines B and C
  作者：Mukund K. Gurjar、Chinmoy Pramanik、Debabrata Bhattasali、C. V. Ramana、Debendra K. Mohapatra

  DOI：10.1021/jo070560h

  日期：2007.8.1

  Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihy-droxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.
• A new approach to the C28 fatty acid chain of the marine natural products schulzeines B and C: a concise diastereoselective total synthesis of(−)-schulzeine B
  作者：Chao Yang、Yu-Hui Bao、Pan Liang、Jian-Liang Ye、Ai-E. Wang、Pei-Qiang Huang

  DOI：10.1016/j.tet.2011.06.023

  日期：2011.8

  the marine natural products schulzeines B and C was established based on the l-tartaric acid derived C4 chiron 11 via successive 1,4-bis-chain elongation reactions and catalytic asymmetric hydrogenation. The chiral tricyclic core 8 was constructed via a diastereoselective Pictet–Spengler cyclization reaction (dr = 89:11) of the l-glutamic acid derived precursor 13. On this basis, a concise total synthesis

  基于1-酒石酸衍生的C 4 chiron 11，通过连续的1，4-双链延长反应和催化不对称氢化作用，建立了对海洋天然产物舒尔西汀B和C的C 28脂肪酸链的对映选择性方法。手性三环核芯8是通过l-谷氨酸衍生的前体13的非对映选择性Pictet-Spengler环化反应（dr  = 89:11）构建的。在此基础上，公开了简明的（-）-舒尔西汀B（5）的全合成。