(6S,7R,8S)-(-)-7-epi-goniodiol | 1152589-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (6S,7R,8S)-(-)-7-epi-goniodiol
• 英文别名: (6S,7R,8S)-goniodiol；(2S)-2-[(1R,2S)-1,2-dihydroxy-2-phenylethyl]-2,3-dihydropyran-6-one
• CAS: 1152589-20-2
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: RTNQVKQMVIXUPZ-DRZSPHRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  生成 (6S,7R,8S)-(-)-7-epi-goniodiol
  参考文献：
  名称：

  Syntheses of All Stereoisomers of Goniodiol from Yeast-Reduction Products and Their Antimicrobiological Activity

  摘要：

  贡碘醇的所有立体异构体都是由酵母还原产物合成的。C-6 手性中心由酵母还原产物的手性中心转化而来。由酵母还原产物制备的烯烃立体选择性地转化为乙二醇，构建了 C-7 和 C-8 立体化学结构。(+)-冈碘二醇和 7-表-(+)-冈碘二醇对中间耶尔森菌的抗菌活性最高（MIC，3.1 毫米）。

  DOI：

  10.1271/bbb.80262

文献信息

• Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6<i>S</i>,7<i>S</i>,8<i>S</i>)-Goniodiol, (−)-Parvistone D, and (+)-Parvistone E
  作者：Perla Ramesh、Tadikamalla P. Rao

  DOI：10.1021/acs.jnatprod.6b00386

  日期：2016.8.26

  A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (−)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72–75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot

  （+）-goniodiol（1），（6 S，7 S，8 S）-goniodiol（2），（-）-parvistone D（4）和（+）-parvistone的无保护基的全合成E（6）从市售反式分子的五步反应中有效地获得了。-肉桂醛具有较高的总收率（72–75％）。合成策略是从拟定的苯乙烯基内酯的生物合成途径中获得启发的。该策略的关键转变包括在水性介质中一氧化碳球蛋白从一锅转化为goniodiol或9-deoxygoniopypyrone，立体选择性环氧化，闭环复分解和立体选择性Maruoka烯丙基化。该路线适合合成各种类似物以进行生物学评估。
• Annulation–retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products
  作者：Qianlan Xu、Jialin Li、Xuemin Li、Lin Hu

  DOI：10.1039/d1cc06207g

  日期：——

  annulation–retro-Claisen cascade, which involves the [4 + 1] or [5 + 1] annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone

  一种新型高效的环化-逆克莱森级联反应，涉及 α-苯甲酰乙酸酯与双亲电子过氧化物的 [4 + 1] 或 [5 + 1] 环化以及随后在温和碱性条件下的脱苯甲酰化过程，已被开发用于快速以良好的收率构建有价值的四氢呋喃-和二氢吡喃-2-羧酸盐。通过采用新反应，γ-和δ-内酯天然产物如(±)-tanikolide、(±)-goniothalamins、(±)-7- epi- goniodiol和(±)-plakolide A的统一全合成分4-7步完成。
• Total synthesis of (±)-9-deoxygoniopypyrone
  作者：Richard W. Friesen、Suzanne Bissada

  DOI：10.1016/s0040-4039(00)77261-3

  日期：1994.8

  The total synthesis of (+/-)-9-deoxygoniopypyrone (1) from the alpha-allenic alcohol 2 is described. The synthesis is accomplished in 10 steps with the relative configuration of the three contiguous asymmetric centers being established by the highly diastereoselective formation of the synvicinal diet 3 via the iodo-cyclofunctionalization reaction of the allenic carbamate 5 and the epoxidation of the olefinic acetonide 11.
• Syntheses of All Stereoisomers of Goniodiol from Yeast-Reduction Products and Their Antimicrobiological Activity
  作者：Takahiro YOSHIDA、Satoshi YAMAUCHI、Ryosuke TAGO、Masafumi MARUYAMA、Koichi AKIYAMA、Takuya SUGAHARA、Taro KISHIDA、Yojiro KOBA

  DOI：10.1271/bbb.80262

  日期：2008.9.23

  All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mm) against Yersinia intermedia.

  贡碘醇的所有立体异构体都是由酵母还原产物合成的。C-6 手性中心由酵母还原产物的手性中心转化而来。由酵母还原产物制备的烯烃立体选择性地转化为乙二醇，构建了 C-7 和 C-8 立体化学结构。(+)-冈碘二醇和 7-表-(+)-冈碘二醇对中间耶尔森菌的抗菌活性最高（MIC，3.1 毫米）。