(2Z,4E,7S,8R,9R,10S)-8,10-dimethyl-7-(triisopropylsilyloxy)-9-[(2E)-3-phenylacryloxy]-dodec-2,4-dienamide | 781642-42-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2Z,4E,7S,8R,9R,10S)-8,10-dimethyl-7-(triisopropylsilyloxy)-9-[(2E)-3-phenylacryloxy]-dodec-2,4-dienamide
• 英文别名: [(3S,4R,5R,6S,8E,10Z)-12-amino-3,5-dimethyl-12-oxo-6-tri(propan-2-yl)silyloxydodeca-8,10-dien-4-yl] (E)-3-phenylprop-2-enoate
• CAS: 781642-42-0
• 化学式: C₃₂H₅₁NO₄Si
• 分子量: 541.847
• InChiKey: UEQSFHHGBHVGNI-FKEACLAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2Z,4E,7S,8R,9R,10S)-8,10-dimethyl-7-(triisopropylsilyloxy)-9-[(2E)-3-phenylacryloxy]-dodec-2,4-dienamide 在 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到bisiliskamide A
  参考文献：
  名称：

  Total Synthesis of Basiliskamides A and B

  摘要：

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).

  DOI：

  10.1021/ol048574m
• 作为产物：
  描述：

  (3S,4R,5R,6S)-4,6-dimethyl-5-methoxymethoxy-3-(triisopropylsilyloxy)-octanal 在 chromium dichloride 、 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 三氯化硼 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 88.0h， 生成 (2Z,4E,7S,8R,9R,10S)-8,10-dimethyl-7-(triisopropylsilyloxy)-9-[(2E)-3-phenylacryloxy]-dodec-2,4-dienamide
  参考文献：
  名称：

  Total Synthesis of Basiliskamides A and B

  摘要：

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).

  DOI：

  10.1021/ol048574m

文献信息

• Total Synthesis of Basiliskamides A and B
  作者：Darren J. Lipomi、Neil F. Langille、James S. Panek

  DOI：10.1021/ol048574m

  日期：2004.9.1

  The first enantioselective synthesis of the polyketide antibiotics basiliskamides A and B, which exhibit potent in vivo activity against Candida albicans and Aspergillus fumigatus, has been achieved. Serial asymmetric crotylsilane and crotylboronate additions established the C7-C10 stereochemical tetrad. Takai iodoolefination and palladium-mediated cross-coupling were used to install the (Z,E)-vinyl acrylamide. Spectroscopic data is consistent with the assignment of the absolute configurations of the natural products as (7S,8S,9R,10S).
• Stereoselective synthesis of basiliskamides A and B via Prins cyclisation
  作者：J.S. Yadav、P. Purushothama Rao、M. Sridhar Reddy、A.R. Prasad

  DOI：10.1016/j.tetlet.2008.07.024

  日期：2008.9

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.