tert-butyl (3S,11bR)-9,11-dihydroxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate | 949463-74-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: tert-butyl (3S,11bR)-9,11-dihydroxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate
• 英文别名: (+)-(3S,11bR)-3-(tert-butoxycarbonylamino)-9,11-dihydroxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one；tert-butyl N-[(3S,11bR)-9,11-dihydroxy-4-oxo-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-3-yl]carbamate
• CAS: 949463-74-5
• 化学式: C₁₈H₂₄N₂O₅
• 分子量: 348.399
• InChiKey: REWMJNVVSQCQLM-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,11bR)-9,11-dihydroxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate 在 盐酸 、 四丁基碘化铵 、 caesium carbonate 、 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 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide
  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
• 作为产物：
  描述：

  methyl (S)-2-(benzyloxycarbonylamino)-5-(3,5-bis(benzyloxy)phenethylamino)-5-oxopentanoate 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 碳酸氢钠 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 17.5h， 生成 tert-butyl (3S,11bR)-9,11-dihydroxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate
  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。
• 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。
• Formal Enantioselective Total Synthesis of Schulzeines A–C via Pd–Catalyzed Intramolecular Asymmetric Allylic Amination
  作者：Chi-Feng Lin、Iwao Ojima

  DOI：10.1021/jo2009615

  日期：2011.8.5

  Formal enantioselective total synthesis of schulzeines A-C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.