(+)-heliconol A | 907198-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-heliconol A
• 英文别名: Heliconol A；(2R,3R,3aS,4S,6aR)-2-nonyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]furan-3,3a,4,6a-tetrol
• CAS: 907198-28-1
• 化学式: C₁₆H₃₀O₅
• 分子量: 302.411
• InChiKey: NMSODLCWHSAFNQ-JKJDWNRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-heliconol A 、 4-溴苯甲酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 4,6-bis(4-bromobenzoyl)heliconol A
  参考文献：
  名称：

  Heliconols A−C:  Antimicrobial Hemiketals from the Freshwater Aquatic Fungus Helicodendron giganteum

  摘要：

  Cultures of the freshwater aquatic fungus Helicodendron giganteum afforded three new compounds, heliconols A-C (1-3), that contain an unusual reduced furanocyclopentane unit. The structures of these metabolites were assigned by analysis of 1D and 2D NMR data. The absolute configuration of heliconol A ( 1) was assigned by single-crystal X-ray crystallographic analysis of its dibromobenzoate derivative. Heliconol A showed antifungal and antibacterial activities in disk diffusion assays.

  DOI：

  10.1021/ol060916w
• 作为产物：
  描述：

  (2R,3R,3aR,4S,6aR)-3a-(tert-butyldimethylsilyloxy)-4-(tert-butyldiphenylsilyloxy)-2-nonyl-hexahydro-2H-cyclopenta[b]furan-3,6a-diol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(+)-heliconol A
  参考文献：
  名称：

  Highly selective approach for the total synthesis of (+)-heliconol A

  摘要：

  The total synthesis of heliconol A, a representative of a new class of polyketide-derived hemiketals containing a reduced furanocyclopentane unit, has been achieved via the stereoselective reduction of a ketone, the face selective dihydroxylation, a Sonogashira coupling reaction, and a cis-selective reduction as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.031