decarestrictine O | 152053-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: decarestrictine O
• 英文别名: (2R,4S,5S,6E,8S)-4,5,8-trihydroxy-2-methyl-2,3,4,5,8,9-hexahydrooxecin-10-one
• CAS: 152053-15-1
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: KYLGPSQYGNCTQJ-XYEXOTNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 41.58h， 生成 decarestrictine O
  参考文献：
  名称：

  A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O

  摘要：

  A facile chiral pool total synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O has been achieved from L-(+)-diethyl tartrate. The strategy utilized is conventional and flexible. Wittig homologation and Grubbs ring closing metathesis are the key reactions employed for the synthesis of the title molecules. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.008

文献信息

• Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9-<i>epi</i>-Stagonolide C Employing Chiral Hexane-1,2,3,5-tetraol Derivatives as Building Blocks
  作者：Krishanu Show、Pradeep Kumar

  DOI：10.1002/ejoc.201600625

  日期：2016.9

  organocatalytic approach to the synthesis of (2R,3S)-hexane-1,2,3,5-tetraol (11) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates 11 were prepared with complete stereocontrol through the proline-catalyzed intermolecular aldol reaction between acetone and d-glyceraldehyde acetonide. The synthetic utility of the

  已开发出一种合成 (2R,3S)-己烷-1,2,3,5-四醇 (11) 衍生物（以不同立体异构体形式并带有不同保护基团）的有机催化方法。关键的手性中间体11是通过丙酮和d-甘油醛缩​​醛之间的脯氨酸催化的分子间醛醇反应在完全立体控制下制备的。通过标准合成方案将中间体转化为标题羟基化吡喃和各种不饱和内酯，证明了中间体的合成效用。
• Stereoselective total synthesis of decarestrictine O
  作者：Jhillu S. Yadav、K. Anantha Lakshmi、N. Mallikarjuna Reddy、Nipunge Swapnil、A. Ramachandra Prasad

  DOI：10.1016/j.tetasy.2012.06.027

  日期：2012.8

  The stereoselective total synthesis of decarestrictine O, a polyketide natural product is described. The synthesis involves MacMillan α-hydroxylation, C1-Wittig olefination, hydrolytic kinetic resolution and ring closing metathesis (RCM) as key steps. Improved efficiency was achieved by using the DIBAL mediated reductive transformation of trans-dimethyl l-tartrate acetonide into ε-hydroxy α,β-unsaturated

  描述了去甲乙胺啶醇（一种聚酮化合物天然产物）的立体选择性全合成。合成过程涉及MacMillanα-羟基化，C 1 -Wittig烯化，水解动力学拆分和闭环复分解（RCM）等关键步骤。通过使用DIBAL介导的一步法将酒石酸二甲酯反式转化为ε-羟基α，β-不饱和酯，可以提高效率。
• First stereoselective total synthesis of decarestrictine O via RCM protocol
  作者：Palakodety Radha Krishna、T. Jagannadha Rao

  DOI：10.1016/j.tetlet.2010.05.064

  日期：2010.8

  A convergent first stereoselective total synthesis of decarestrictine O via RCM protocol starting from 1,3-propanediol and propylene oxide is reported.

  据报道，从1，3-丙二醇和环氧丙烷开始，通过RCM协议，对脱卡因汀O进行了聚合的第一立体选择性全合成。
• A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O
  作者：Kuchena Vamshikrishna、Garlapati Srinu、Pabbaraja Srihari

  DOI：10.1016/j.tetasy.2013.12.008

  日期：2014.2

  A facile chiral pool total synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O has been achieved from L-(+)-diethyl tartrate. The strategy utilized is conventional and flexible. Wittig homologation and Grubbs ring closing metathesis are the key reactions employed for the synthesis of the title molecules. (C) 2013 Elsevier Ltd. All rights reserved.