(S)-(E)-4-(tributylstannyl)but-3-en-2-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(E)-4-(tributylstannyl)but-3-en-2-ol
• 化学式: C₁₆H₃₄OSn
• 分子量: 361.155
• InChiKey: JDGHITRWXNGSKV-NDNWHDOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(E)-4-(tributylstannyl)but-3-en-2-ol 在 碘 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 以64%的产率得到(S,E)-4-iodobut-3-en-2-ol
  参考文献：
  名称：

  Total Syntheses of the Dihydrofuranonecarboxylate Natural Products Gregatin B and E: Gram-Scale Synthesis of (+)-Gregatin B and Unambiguous Assignment of the Stereostructure of (+)-Gregatin E

  摘要：

  We synthesized the dextrorotatory enantiomers of gregatin B (1.3 g scale) and E, establishing their diene side chains in the last step by Heck coupling with variable iodoolefins. Their counterpart was synthesized in 30% overall yield and with high enantiopurity (97% ee) from benzyl tiglate, beginning with an asymmetric dihydroxylation. The stereostructure of gregatin E followed from HPLC comparisons between the four synthetic stereoisomers of this compound and natural gregatin E, which we isolated from Cadophora gregata.

  DOI：

  10.1021/ol5032602
• 作为产物：
  描述：

  (S)-(-)-3-丁炔-2-醇 、 三正丁基氢锡 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以73%的产率得到(S)-(E)-4-(tributylstannyl)but-3-en-2-ol
  参考文献：
  名称：

  Total Syntheses of the Dihydrofuranonecarboxylate Natural Products Gregatin B and E: Gram-Scale Synthesis of (+)-Gregatin B and Unambiguous Assignment of the Stereostructure of (+)-Gregatin E

  摘要：

  We synthesized the dextrorotatory enantiomers of gregatin B (1.3 g scale) and E, establishing their diene side chains in the last step by Heck coupling with variable iodoolefins. Their counterpart was synthesized in 30% overall yield and with high enantiopurity (97% ee) from benzyl tiglate, beginning with an asymmetric dihydroxylation. The stereostructure of gregatin E followed from HPLC comparisons between the four synthetic stereoisomers of this compound and natural gregatin E, which we isolated from Cadophora gregata.

  DOI：

  10.1021/ol5032602

文献信息

• A New, Iterative Strategy for the Synthesis of Unsymmetrical Polyynes:  Application to the Total Synthesis of 15,16-Dihydrominquartynoic Acid
  作者：Sanghee Kim、Shinae Kim、Taeho Lee、Hyojin Ko、Deukjoon Kim

  DOI：10.1021/ol0484963

  日期：2004.9.1

  [reaction: see text] A new iterative strategy for the synthesis of unsymmetrically substituted polyynes has been developed. The starting bromoalkyne is homologated by one acetylene unit through palladium-catalyzed cross-coupling with a TIPS-protected terminal acetylene and a subsequent in situ one-pot AgF-mediated desilylative bromination. The utility of this new synthetic method is demonstrated by

  [反应：见正文]已开发出一种用于合成不对称取代的多炔的新迭代策略。起始的溴炔由一个乙炔单元通过钯催化的与TIPS保护的末端乙炔的交叉偶联和随后的原位一锅AgF介导的脱甲硅烷基化的溴化而同系化。这种新的合成方法的实用性通过将其应用于（S）-（E）-15,16-二氢亚甲基季戊二酸的全合成得到证明。
• Stereoselective Total Synthesis of (−)-Perrottetinene and Assignment of Its Absolute Configuration
  作者：Yanling Song、Soonho Hwang、Ping Gong、Deukjoon Kim、Sanghee Kim

  DOI：10.1021/ol702692q

  日期：2008.1.1

  The first stereoselective total synthesis of the bibenzyl tetrahydrocannabinol, (-)-perrottetinene, has been achieved from readily available starting materials. The absolute stereochemistry is derived from a chiral gamma-hydroxy vinylstannane. The key reaction is the synthesis of the cis-disubstituted cyclohexene ring of perrottetinene by diastereoselective Ireland-Claisen rearrangement and a ring-closing

  联苄四氢大麻酚（-）-perrottetinene的第一个立体选择性全合成已从容易获得的起始原料中获得。绝对立体化学衍生自手性γ-羟基乙烯基锡烷。关键反应是通过非对映选择性爱尔兰-克莱森重排和闭环易位反应合成perrottetinene的顺式-二取代的环己烯环。提出了（-）-perrottetinene的绝对构型。
• Solid-Phase Library Synthesis of Polyynes Similar to Natural Products
  作者：Seonwoo Lee、Taeho Lee、Yun Mi Lee、Deukjoon Kim、Sanghee Kim

  DOI：10.1002/anie.200703208

  日期：2007.11.12
• Total Syntheses of the Dihydrofuranonecarboxylate Natural Products Gregatin B and E: Gram-Scale Synthesis of (+)-Gregatin B and Unambiguous Assignment of the Stereostructure of (+)-Gregatin E
  作者：Fabian Weber、Reinhard Brückner

  DOI：10.1021/ol5032602

  日期：2014.12.19

  We synthesized the dextrorotatory enantiomers of gregatin B (1.3 g scale) and E, establishing their diene side chains in the last step by Heck coupling with variable iodoolefins. Their counterpart was synthesized in 30% overall yield and with high enantiopurity (97% ee) from benzyl tiglate, beginning with an asymmetric dihydroxylation. The stereostructure of gregatin E followed from HPLC comparisons between the four synthetic stereoisomers of this compound and natural gregatin E, which we isolated from Cadophora gregata.