(+)-deacetylkumausine | 88034-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-deacetylkumausine
• 英文别名: trans-deacetylkumausyne；(2R,3R,5R)-5-((R,E)-1-bromohex-3-enyl)-2-((E)-pent-2-en-4-ynyl)tetrahydrofuran-3-ol；(2R,3R,5R)-5-[(E,1R)-1-bromohex-3-enyl]-2-[(E)-pent-2-en-4-ynyl]oxolan-3-ol
• CAS: 88034-95-1
• 化学式: C₁₅H₂₁BrO₂
• 分子量: 313.235
• InChiKey: RMJPNJYVWXJAHL-ZZBMQANISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-deacetylkumausine 在 氢气 作用下， 生成 (2R,3R,5R)-5-((R)-1-Bromo-hexyl)-2-pentyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  KUMAUSYNES AND DEACETYLKUMAUSYNES, FOUR NEW HALOGENATED C-15 ACETYLENES FROM THE RED ALGALAURENCIA NIPPONICAYAMADA

  摘要：

  从红藻L. nipponica Yamada中分离出四种新的卤代C

  DOI：

  10.1246/cl.1983.1643
• 作为产物：
  描述：

  (3aR,5R,6aR)-5-[(1S)-1-hydroxybut-3-en-1-yl]tetrahydrofuro[3,2-b]furan-2(3H)-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 、 2,6-二叔丁基吡啶 、 四溴化碳 、 二异丁基氢化铝 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 22.92h， 生成 (+)-deacetylkumausine
  参考文献：
  名称：

  Stereoselective Total Synthesis of (−)-Kumausallene

  摘要：

  A stereoselective total synthesis of (-)-kumausallene was completed in 12 steps from acetylacetone. The hidden symmetry of (-)-kumausallene was recognized, and its skeleton was constructed efficiently from a C(2)-symmetric diol by a palladium-catalyzed cascade reaction. High diastereoselectivity was observed for the DMF-promoted biomimetic 1,4-bromocyclization of a conjugated enyne.

  DOI：

  10.1021/ol201477u

文献信息

• A formal total synthesis of (−)-kumausallene
  作者：Shyamsundar Das、Chepuri V. Ramana

  DOI：10.1016/j.tet.2015.09.027

  日期：2015.11

  Deacetylkumausyne—a penultimate intermediate in Tang's total synthesis of (−)-kumausallene has been synthesized employing a chiral pool approach and thus culminating in a formal total synthesis of kumausallene. The opening of an epoxide with alkyne (use of Birch reduction for the selective construction of E-pent-3-enyl group) and C-allylation have been used to introduce the pendant alkenyl side chains

  脱乙酰基尿嘧啶-唐氏（-）-kumausallene的总合成中的倒数第二个中间体，已采用手性池方法合成，从而最终形成了kumausallene的正式总合成。环氧化物与炔开口（使用Birch还原为选择性构造的Ë -戊-3-烯基团）和C-烯丙基化已被用于引入侧烯侧链。初始试图执行到汤的路线的替代包括经由bromoetherification和随后的S中的bromoallene单元的先前安装Ñ2位移是不成功的。为了克服这个问题，另一种方法是开发在Deacetylkumausyne（已合成和表征唐小组其他天然产物）到达。由此，该总锻炼最终导致了一个正式的全合成（ - ） - kumausallene。
• Biomimetic-Type Synthesis of Halogenated Tetrahydrofurans from <i>Laurencia</i>. Total Synthesis of <i>trans</i>-(+)-Deacetylkumausyne
  作者：Tomás Martín、Marcos A. Soler、Juan M. Betancort、Victor S. Martín

  DOI：10.1021/jo962135m

  日期：1997.3.1
• Total Synthesis of (−)-trans-Kumausyne
  作者：K Osumi

  DOI：10.1016/00404-0399(50)1100v-

  日期：1995.8.7

  The total synthesis of (-)-trans-kumausyne has been accomplished in an enantiospecific fashion starting from an L-arabinose derivative. The key step is the stereoselective formation of the substituted tetrahydrofuran via novel cyclization of the beta-silyl cation intermediate, generated by the addition of allylsilane to di-O-isopropylidene-aldehydo-arabinose in the presence of boron trifluoride etherate.
• Stereoselective Total Synthesis of (−)-Kumausallene
  作者：Jenny B. Werness、Weiping Tang

  DOI：10.1021/ol201477u

  日期：2011.7.15

  A stereoselective total synthesis of (-)-kumausallene was completed in 12 steps from acetylacetone. The hidden symmetry of (-)-kumausallene was recognized, and its skeleton was constructed efficiently from a C(2)-symmetric diol by a palladium-catalyzed cascade reaction. High diastereoselectivity was observed for the DMF-promoted biomimetic 1,4-bromocyclization of a conjugated enyne.
• KUMAUSYNES AND DEACETYLKUMAUSYNES, FOUR NEW HALOGENATED C-15 ACETYLENES FROM THE RED ALGA<i>LAURENCIA NIPPONICA</i>YAMADA
  作者：Teruaki Suzuki、Kuniko Koizumi、Minoru Suzuki、Etsuro Kurosawa

  DOI：10.1246/cl.1983.1643

  日期：1983.10.5

  Four new halogenated C15-nonterpenoids which are unusual oxolane derivatives have been isolated from the red alga L. nipponica Yamada, and their structures were determined by spectral and chemical evidence.

  从红藻L. nipponica Yamada中分离出四种新的卤代C