(Z)-(S)-9-[(1R,2R)-2-((E)-(R)-4-Hydroxy-non-2-enoyl)-cyclopropyl]-4,5,8,9-tetrahydro-3H-oxonin-2-one | 164524-14-5

• 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: (Z)-(S)-9-[(1R,2R)-2-((E)-(R)-4-Hydroxy-non-2-enoyl)-cyclopropyl]-4,5,8,9-tetrahydro-3H-oxonin-2-one
• CAS: 164524-14-5
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: OSCBXIDLVXYCKD-SODXPYFYSA-N

反应信息

• 作为反应物：
  描述：

  (Z)-(S)-9-[(1R,2R)-2-((E)-(R)-4-Hydroxy-non-2-enoyl)-cyclopropyl]-4,5,8,9-tetrahydro-3H-oxonin-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以40%的产率得到(Z)-(S)-9-[(1R,2R)-2-((E)-(R)-1,4-Dihydroxy-non-2-enyl)-cyclopropyl]-4,5,8,9-tetrahydro-3H-oxonin-2-one
  参考文献：
  名称：

  卤代内酯和新卤代内酯的总不对称合成

  摘要：

  据报道已经完成了海洋天然产物卤代内酯和新卤代内酯的第一个全合成反应。关键步骤是乙烯基阴离子和醛之间的中等立体选择性偶联。还报道了由于近端羟基的存在而出乎意料的缓慢的甲硅烷基化。

  DOI：

  10.1016/0040-4039(95)00588-4
• 作为产物：
  描述：

  (Z)-(S)-9-{(1R,2R)-2-[(E)-(R)-4-(tert-Butyl-diphenyl-silanyloxy)-non-2-enoyl]-cyclopropyl}-4,5,8,9-tetrahydro-3H-oxonin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到(Z)-(S)-9-[(1R,2R)-2-((E)-(R)-4-Hydroxy-non-2-enoyl)-cyclopropyl]-4,5,8,9-tetrahydro-3H-oxonin-2-one
  参考文献：
  名称：

  卤代内酯和新卤代内酯的总不对称合成

  摘要：

  据报道已经完成了海洋天然产物卤代内酯和新卤代内酯的第一个全合成反应。关键步骤是乙烯基阴离子和醛之间的中等立体选择性偶联。还报道了由于近端羟基的存在而出乎意料的缓慢的甲硅烷基化。

  DOI：

  10.1016/0040-4039(95)00588-4

文献信息

• Total Synthesis of Halicholactone and Neohalicholactone¹
  作者：Douglas J. Critcher、Stephen Connolly、Martin Wills

  DOI：10.1021/jo962312j

  日期：1997.9.1

  The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.