sundiversifolide | 935875-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: sundiversifolide
• 英文别名: (3S,3aR,7S,8aR)-3,3a,4,7,8,8a-Hexahydro-6-(2-hydroxyethyl)-3,7-dimethyl-2H-cyclohepta[b]furan-2-one；(3S,3aR,7S,8aR)-6-(2-hydroxyethyl)-3,7-dimethyl-3,3a,4,7,8,8a-hexahydrocyclohepta[b]furan-2-one
• CAS: 935875-77-7
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: MOXJTUNOIGNZKZ-GAIPPQHRSA-N

物化性质

• 熔点：
  42-47 °C
• 沸点：
  380.1±42.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-环庚二烯 在 2,2,6,6-四甲基哌啶 、 咪唑 、 1‐methyl‐2‐azaadamantane‐N‐oxyl 、 deMeQDAc 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 dirhodium tetraacetate 、 copper(l) iodide 、 正丁基锂 、 对甲苯磺酰叠氮 、 碘苯二乙酸 、 2,6-二苯基苯酚 、 羟基甲苯磺酰碘苯 、 5%-palladium/activated carbon 、 四丁基氟化铵 、 氢气 、 三甲基铝 、 氧气 、 sodium acetate 、 tetraphenylporphyrin 、 L-Selectride 、 二异丁基氢化铝 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 二异丙胺 、 N,N-二异丙基乙胺 、 苯酚 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 165.0h， 生成 sundiversifolide
  参考文献：
  名称：

  Concise Entry to Both Enantiomers of 8-Oxabicyclo[3.2.1]oct-3-en-2-one Based on Novel Oxidative Etherification: Formal Synthesis of (+)-Sundiversifolide

  摘要：

  Both enantiomers of 8-oxabicyclo[3.2.1]oct-3-en-2-one (6) have been synthesized from 4-hydroxycyclohept-2-enone (3) on the basis of a novel oxidative cyclo-etherification using PhI(OH)OTs (Koser's reagent). (-)-(1S,5R)-8-Oxabicyclo[3.2.1]oct-3-en-2-one [(-)-6, 95% ee] was expeditiously transformed to (-)-sundiversifolide (1).

  DOI：

  10.1021/ol201273b

文献信息

• Enantioselective and Collective Syntheses of Xanthanolides Involving a Controllable Dyotropic Rearrangement of cis-β-Lactones
  作者：Weiwu Ren、Yichao Bian、Ziyang Zhang、Hai Shang、Pengtao Zhang、Yuejie Chen、Zhen Yang、Tuoping Luo、Yefeng Tang

  DOI：10.1002/anie.201202643

  日期：2012.7.9

  atom‐economic, enantio‐, and diastereoselective synthetic route to trisubstituted γ‐butyrolactones based on a Wagner–Meerwein‐type dyotropic rearrangement of cis‐β‐lactones is described (see scheme). This methodology was applied in efficient and protecting‐group‐free formal syntheses and total syntheses of various xanthanolide natural products.

  让我们交换一下：描述了一种基于Wagner-Meerwein型顺式-β-内酯重排的可扩展，原子经济，对映和非对映选择性的合成三取代γ-丁内酯的方法（参见方案）。该方法学被用于各种黄原醇天然产物的高效且无保护基团的形式合成和总合成中。
• Total Synthesis of (+)- and (−)-Sundiversifolide via Intramolecular Acylation and Determination of the Absolute Configuration
  作者：Keiko Ohtsuki、Kazumasa Matsuo、Takashi Yoshikawa、Chihiro Moriya、Kaori Tomita-Yokotani、Kozo Shishido、Mitsuru Shindo

  DOI：10.1021/ol8001333

  日期：2008.3.1

  Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The gamma-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic alpha-hydroxyhemiacetal with Ph3P=CMe(CO2R).

  有机锂的分子内酰化导致sundiversifolide的两个对映异构体的有效立体控制的全合成。通过HPLC分析和化感作用测定法确定绝对构型。通过将双环α-羟基半缩醛与Ph3P = CMe（CO2R）缩合获得由丁烯内酯产生的gamma-lactone部分。
• Total Synthesis of (+)-Sundiversifolide
  作者：Hiromasa Yokoe、Hiroyuki Sasaki、Tomoyuki Yoshimura、Mitsuru Shindo、Masahiro Yoshida、Kozo Shishido

  DOI：10.1021/ol062960h

  日期：2007.3.1

  The first, enantiocontrolled total synthesis of (+)-sundiversifolide has been accomplished using the sequential ring-closing metathesis, [3,3]sigmatropic rearrangement, and iodolactonization for the key assembly of the cis-fused oxabicyclo[5.3.0] decene framework of the natural product.
• Total synthesis of xanthanolides
  作者：Kazumasa Matsuo、Keiko Ohtsuki、Takashi Yoshikawa、Kozo Shishido、Kaori Yokotani-Tomita、Mitsuru Shindo

  DOI：10.1016/j.tet.2010.08.061

  日期：2010.10

  The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), dihydroxanthatin (2), and xanthatin (3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide. (C) 2010 Elsevier Ltd. All rights reserved.
• Concise Entry to Both Enantiomers of 8-Oxabicyclo[3.2.1]oct-3-en-2-one Based on Novel Oxidative Etherification: Formal Synthesis of (+)-Sundiversifolide
  作者：Muneo Kawasumi、Naoki Kanoh、Yoshiharu Iwabuchi

  DOI：10.1021/ol201273b

  日期：2011.7.15

  Both enantiomers of 8-oxabicyclo[3.2.1]oct-3-en-2-one (6) have been synthesized from 4-hydroxycyclohept-2-enone (3) on the basis of a novel oxidative cyclo-etherification using PhI(OH)OTs (Koser's reagent). (-)-(1S,5R)-8-Oxabicyclo[3.2.1]oct-3-en-2-one [(-)-6, 95% ee] was expeditiously transformed to (-)-sundiversifolide (1).