(-)-wodeshiol | 58007-97-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (-)-wodeshiol
• 英文别名: wodeshiol；kigeliol；(3R,3aS,6R,6aS)-3,6-bis(1,3-benzodioxol-5-yl)-1,3,4,6-tetrahydrofuro[3,4-c]furan-3a,6a-diol
• CAS: 58007-97-9
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: IPWXMGAKBVCNDA-ZRNYENFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-wodeshiol 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 以60 mg的产率得到胡椒酸
  参考文献：
  名称：

  柯林斯的心木中的新木脂素

  摘要：

  据报道，从Cleistanthus collinus的心材中分离并鉴定了五种新化合物和九种已知化合物。这些新化合物是wodeshiol 16，3,4- dihydrotaiwaninÇ 20，和三个新的苷24，25和26山荷叶素的和taiwanin E中的1 H和13这些化合物的C NMR谱也报道。

  DOI：

  10.1016/s0040-4020(01)98893-3
• 作为产物：
  描述：

  (R)-1,3-benzodioxol-5-yl-[(2S)-2-[(2S)-2-[(R)-1,3-benzodioxol-5-yl(hydroxy)methyl]oxiran-2-yl]oxiran-2-yl]methanol 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 22.0h， 以61%的产率得到(-)-wodeshiol
  参考文献：
  名称：

  A Catalytic Enantioselective Total Synthesis of (−)-Wodeshiol

  摘要：

  [GRAPHICS](-)-Wodeshiol of >99% ee has been synthesized from the alpha,beta-enone shown using a number of noteworthy steps including a novel C-C coupling reaction.

  DOI：

  10.1021/ol991151d

文献信息

• An efficient asymmetric synthesis of (–)-wodeshiol
  作者：SOON HO LEE、JAE-CHUL JUNG、OEE SOOK PARK

  DOI：10.1007/s12039-011-0078-3

  日期：2011.5

  An efficient synthesis of (–)-wodeshiol 1 is described. The key reactions include highly stereoselective aldol condensation of piperonal with the dianion of chiral oxazolidinone, subsequent intramolecular ring cyclization of the aldol product 8 and a diastereocontrolled oxygenation of dilactone 7 in good yield.

  描述了（-）-wodeshiol 1的有效合成。关键反应包括的胡椒醛高立体选择性的醛醇缩合与手性恶唑烷酮，羟醛产物的后续的分子内环的环化的二价阴离子8和双内酯的diastereocontrolled氧合7以良好的收率。
• A naphthoquinone and a lignan from the wood of Kigelia pinnata
  作者：Kenichiro Inoue、Hiroyuki Inouye、Cheng-Chang Chen

  DOI：10.1016/0031-9422(81)80128-8

  日期：1981.1

  Abstract A new naphthoquinone, kigelinone, and a new lignan, kigeliol, together with six known constituents including lapachol and dehydro-α- lapachone, were isolated from the wood of Kigelia pinnata . On the basis of spectral data and chemical degradations, kigelinone was characterized as 2-(1-hydroxyethyl)-8-hydroxy-naphtho[2,3-b]furano-4,9-dione and kigeliol as (2 S ,6 S )-bis(3,4-methylenedioxyphenyl)-

  摘要 从Kigelia pinnata 木材中分离到了一种新的萘醌-kigelinone 和一种新的木脂素-kigeliol，以及六种已知成分，包括lapachol 和dehydro-α-lapachone。根据光谱数据和化学降解，kigelinone 被表征为 2-(1-hydroxyethyl)-8-hydroxy-naphtho[2,3-b]furano-4,9-dione，kigeliol 被表征为 (2 S ,6 S )-双(3,4-亚甲基二氧基苯基)-3,7-二氧杂双环[3.3.0]辛烷-1 R ,5 R -二醇或其对映异构体。
• Transformations of lignans. Part 10: Acid-catalysed rearrangements of arboreol and wodeshiol and conversion of gmelanone oxime into a dihydropyranone derivative
  作者：Revuru Venkateswarlu、Chakicherla Kamakshi、Pithani V. Subhash、Syed G.A. Moinuddin、Mangala P. Gowri、Robert S. Ward、Andrew Pelter、Michael B. Hursthouse、Simon J. Coles、Mark E. Light

  DOI：10.1016/j.tet.2005.06.106

  日期：2005.9

  gmelanone 2 by a pinacol-type rearrangement of arboreol 1 supports its biogenesis and confirms its relative and absolute configuration. The further transformation of gmelanone oxime 12 into the dihydropyranone oxime 13 supports the intermediacy of gmelanone like intermediates in the rearrangements of furofuran lignans to pyran derivatives. In contrast, acid-catalysed rearrangement of wodeshiol 7 affords the

  gmelanone的合成2通过arboreol的频哪醇型重排1和支撑其的生物合成，并确认它的相对和绝对构型。葛兰酮肟12进一步转化为二氢吡喃酮肟13支持了呋喃呋喃木脂素向吡喃衍生物的重排时，中间物像中间物一样与葛兰酮类似。相反，wodeshiol 7的酸催化重排得到二氢吡喃酮8。
• Rearrangements of 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans reactions of paulownin and wodeshiol with triethylsilane and BF3-etherate
  作者：Andrew Pelter、Robert S. Ward、Revuru Venkateswarlu、Chakicherla Kamakshi

  DOI：10.1016/s0040-4020(01)88261-2

  日期：1992.1

  Paulownin on treatment with triethylsilane and BF3-etherate reacts in a similar manner to gmelinol, giving an aryltetralin as the product. In contrast, wodeshiol under the same conditions rearranges to two isomeric tetrahydropyran derivatives, the structures of which have been deduced on the basis of their 1H and 13C n.m.r. spectra, including NOE and spin decoupling experiments.

  用三乙基硅烷和BF 3-醚酸酯处理的泡桐素的反应方式与醇二甲酚相似，得到芳基四氢萘为产物。相比之下，沃得舒醇在相同条件下重排为两种异构的四氢吡喃衍生物，其结构是根据其1 H和13 C nmr光谱推导的，包括NOE和自旋解偶联实验。
• Acid catalysed rearrangements of arboreol: A biomimetic synthesis of gmelanone
  作者：L. Ramachandra Row、Reveru Ventkateswarlu、Andrew Pelter、Robert S. Ward

  DOI：10.1016/s0040-4039(00)78645-x

  日期：1980.1