(15R,16R,19S,20S,34S)-cis-solamin | 158705-59-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (15R,16R,19S,20S,34S)-cis-solamin
• 英文别名: cis-solamin A；cis-solamin；(2S)-4-[(13R)-13-hydroxy-13-[(2R,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
• CAS: 158705-59-0
• 化学式: C₃₅H₆₄O₅
• 分子量: 564.89
• InChiKey: RBSBTRALZZSVBA-DIPXFSDISA-N

物化性质

• 熔点：
  63-66 °C
• 沸点：
  683.2±25.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  40
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (15R,16R,19S,20S,34S)-cis-solamin 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以90%的产率得到
  参考文献：
  名称：

  Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I

  摘要：

  A convergent total synthesis of cis-solamin (1a) and its diastereomer (1b) was accomplished. A key reaction of this approach was the use of VO(acac)(2)-catalyzed diastereoselective epoxidation of (Z)-bis-homoallylic alcohol 3 followed by spontaneous cyclization for the cis-THF ring formation. By comparison of the optical rotation of the two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a. Inhibitory action of synthetic 1a and 1b with bovine heart mitochondrial complex I are reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.011
• 作为产物：
  描述：

  反,反,反-1,5,9-环十二烷基三烯 在 ruthenium trichloride 、 四氧化锇 、 四丙基高钌酸铵 、 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 正丁基锂 、 Lipase Amano AK 、 氢氟酸 、 水 、 sodium acetate 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 57.5h， 生成 (15R,16R,19S,20S,34S)-cis-solamin
  参考文献：
  名称：

  顺式索拉明的全合成：利用RuO4催化的二烯氧化环化反应。

  摘要：

  [结构：见正文]使用高度非对映选择性的四氧化钌催化的氧化环化反应作为关键的转化反应，完成了顺式鞘氨醇的对映选择性全合成。进一步的关键步骤涉及酶促脱对称，TPAP催化的氧化末端分化和钌催化的Alder-ene反应。因此，以11个步骤完成了顺式索拉明的总合成，总收率为7.5％。

  DOI：

  10.1021/ol060520k

文献信息

• Total Synthesis and Preliminary Biological Evaluation of <i>cis</i>-Solamin Isomers
  作者：Alex R. L. Cecil、Yulai Hu、María J. Vicent、Ruth Duncan、Richard C. D. Brown

  DOI：10.1021/jo049909g

  日期：2004.5.1

  An efficient total synthesis of cis-solamin (1) has been achieved in 21% overall yield and with a longest linear sequence of just 11 steps from aldehyde 8. A key feature of the approach was the use of asymmetric permanganate-promoted oxidative cyclization to introduce four of the five required stereocenters in a single step. The use of robust and chemoselective methodology meant that the use of protecting

  高效的顺式索拉明（1）的总合成已实现21％的总收率和最长的线性序列，距离醛8仅11个步骤。该方法的主要特点是使用不对称高锰酸盐促进的氧化环化反应，可在一个步骤中引入五个所需的立体中心中的四个。中使用耐用和化学选择性的方法指的是使用保护基团的可能的组装时，能够避免顺-solamin（1）从所述三个片段23，6，和4。该方法还适用于三种其他顺式-solamin异构体的合成2，ent - 1和ent - 2。据报道，顺式索拉明异构体和合成中间体具有细胞毒性和溶血特性。
• Total synthesis of cis-solamin A, a mono-tetrahydrofuran acetogenin isolated from Annona muricata
  作者：Hiroyuki Konno、Yasuhiro Okuno、Hidefumi Makabe、Kazuto Nosaka、Akio Onishi、Yoshinari Abe、Atsuya Sugimoto、Kenichi Akaji

  DOI：10.1016/j.tetlet.2007.11.190

  日期：2008.1

  Total synthesis of cis-solamin A was accomplished without using protecting groups starting from (-)-muricatacin in 11 steps with an overall yield of 4.5%. The backbone of cis-solamin A was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of solamin type mono-THF acetogenins using cross-metathesis
  作者：Hiroyuki Konno、Hidefumi Makabe、Yasunao Hattori、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2010.08.028

  日期：2010.10

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of <i>cis-</i>Solamin Using a Permanganate-Mediated Oxidative Cyclization
  作者：Alexander R. L. Cecil、Richard C. D. Brown

  DOI：10.1021/ol026669n

  日期：2002.10.1

  [GRAPHICS]cis-Solamin (1) and its diastereoisomer 14 have been synthesized in 13 steps using the diastereoselective permanganate-promoted oxidative cyclization of 1,5-dienes to create the tetrahydrofuran diol core. Notably, no protecting groups are required during the stages of fragment assembly.
• Total Synthesis of <i>cis</i>-Solamin
  作者：Hidefumi Makabe、Yasunao Hattori、Akira Tanaka、Takayuki Oritani

  DOI：10.1021/ol0102803

  日期：2002.4.1

  [GRAPHICS]A convergent total synthesis of cis-solamin and its diastereomer was accomplished using VO(acac)(2)-catalyzed diastereoselective epoxidation followed by cyclization of bis-homoallylic alcohol as the key step. By comparison of the optical rotation of two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a.